Chiral Separation System

A system for separation of enantiomers includes a column packed with a stationary phase; a magnetic field generator generating a magnetic field, within which the column is placed, and the magnetic field interacts with the enantiomers as the enantiomers elute through the column with a mobile phase; and a control unit, in communication with the magnetic field generator and the column, to adjust the strength and direction of the magnetic field to separate the enantiomers. 1. A system for separation of enantiomers , comprising:a column packed with a stationary phase;a magnetic field generator to generate a magnetic field, within which the column is placed, and the magnetic field interacting with the enantiomers as the enantiomers elute through the column with a mobile phase; anda control unit in communication with the magnetic field generator and the column to adjust the strength and direction of the magnetic field to separate the enantiomers.2. The system of claim 1 , wherein the magnetic field generator comprises at least one solenoid claim 1 , at least one permanent magnet claim 1 , a superconducting magnet claim 1 , or any other suitable magnetic field generator.3. The system of claim 1 , wherein the magnetic field is a static magnetic field.4. The system of claim 1 , wherein the strength of the magnetic field is adjusted to induce a magnetic dipole in each of the enantiomers and to align the induced magnetic dipole with the magnetic field.5. The system of claim 1 , wherein the direction of the magnetic field is adjusted by varying an angle or a distance claim 1 , or both thereof claim 1 , between the magnetic filed and the column.6. The system of claim 1 , wherein the stationary phase comprises a ferromagnetic material.7. The system of claim 6 , wherein the ferromagnetic material comprises FeOnanocrystals having a size of smaller than 1000 nm.8. The system of claim 1 , wherein the column is a C18 claim 1 , monolithic claim 1 , ion exchange claim 1 , hydrophilic ...

SEPARATING AGENT FOR OPTICAL ISOMERS

Provided is a separating agent for optical isomers, which is configured of a novel xylan derivative and a carrier. Specifically provided is a separating agent for optical isomers, which is configured of a carrier and a xylan-phenylcarbamate derivative that is obtained by substituting a hydroxy group of xylan with a group represented by formula (I) or (II). (In formula (I), R1 represents a halogen or an alkyl group having 1-5 carbon atoms; and the position of substitution of the R1 moiety is the meta position or the para position. In formula (II), each of R2 and R3 independently represents a halogen or an alkyl group having 1-5 carbon atoms, and R2 and R3 are groups different from each other.) 2. The separating agent for optical isomers according to claim 1 , wherein the groups that substitute the hydroxyl groups in the xylan are groups represented by formula (I) claim 1 , and Ris an alkyl group having 1 to 5 carbon atoms.3. The separating agent for optical isomers according to claim 2 , wherein the Rsubstitution position is a meta position claim 2 , and Ris a methyl group or an ethyl group.4. The separating agent for optical isomers according to claim 1 , wherein the groups that substitute the hydroxyl groups in the xylan are groups represented by formula (II) claim 1 , and in formula (II) claim 1 , Ris a halogen and Ris an alkyl group having 1 to 5 carbon atoms.5. The separating agent for optical isomers according to claim 4 , wherein Ris chlorine and Ris a methyl group or an ethyl group.6. The separating agent for optical isomers according to claim 1 , wherein the carrier is silica gel. The present invention relates to a separating agent for optical isomers, and specifically relates to a separating agent for optical isomers, which has a structure in which hydroxyl groups in xylan are substituted with carbamate derivatives having specific structures.Optical isomers are used as medicines and raw materials thereof. In such applications that act on living bodies, it ...

PROCESSES FOR THE RESOLUTION OF BENZODIAZEPIN-2-ONE AND BENZOAZEPIN-2-ONE DERIVATIVES

The present invention relates to processes and intermediates useful in the preparation of biologically active molecules, especially in the synthesis of Respiratory Syncytial Virus (RSV) inhibitors. The present invention also relates to processes and intermediates for the preparation of compounds of Formula (I-0) and Formula (I): 3. The process of claim 1 , wherein X is N.4. The process of claim 1 , wherein X is CH.5. The process of claim 1 , wherein step (a) is carried out in a solvent selected from acetonitrile claim 1 , methanol claim 1 , tetrahydrofuran claim 1 , 2-methyltetrahydrofuran claim 1 , ethyl acetate claim 1 , 1 claim 1 ,2-dimethoxyethane claim 1 , dichloromethane claim 1 , 1 claim 1 ,4-dioxane claim 1 , toluene claim 1 , anisole claim 1 , ethanol claim 1 , acetone claim 1 , N claim 1 ,N-dimethylformamide claim 1 , N claim 1 ,N-dimethylacetamide claim 1 , pyridine and isopropyl acetate or a combination of two or more thereof.6. The process of claim 5 , wherein step (a) is carried out in a solvent selected from tetrahydrofuran and 1 claim 5 ,4-dioxane.7. The process of claim 1 , wherein in step (b) claim 1 , the base is sodium hydroxide claim 1 , potassium carbonate claim 1 , ammonium hydroxide claim 1 , potassium phosphate tribasic or sodium carbonate.8. The process of claim 7 , wherein the base is 1 N sodium hydroxide claim 7 , 5 wt % potassium carbonate claim 7 , 28-30% ammonium hydroxide claim 7 , 10 wt % potassium phosphate tribasic or 5 wt % sodium carbonate.9. The process of claim 1 , wherein in step (a) the compound of Formula (I′) is in a mixture with its enantiomer.10. The process of claim 9 , wherein the mixture is a racemic mixture.13. The process of claim 11 , wherein X is N.14. The process of claim 10 , wherein X is CH.15. The process of claim 11 , wherein step (a) is carried out in a solvent selected from acetonitrile claim 11 , methanol claim 11 , tetrahydrofuran claim 11 , 2-methyltetrahydrofuran claim 11 , ethyl acetate claim 11 , 1 ...

PROCESSES FOR THE RESOLUTION OF BENZODIAZEPIN-2-ONE AND BENZOAZEPIN-2-ONE DERIVATIVES

The present invention relates to processes and intermediates useful in the preparation of biologically active molecules, especially in the synthesis of Respiratory Syncytial Virus (RSV) inhibitors. The present invention also relates to processes and intermediates for the preparation of compounds of Formula (I-0) and Formula (I): 3. The process of claim 1 , wherein X is N.4. The process of claim 1 , wherein X is CH.5. The process of claim 1 , wherein step (a) is carried out in a solvent selected from acetonitrile claim 1 , methanol claim 1 , tetrahydrofuran claim 1 , 2-methyltetrahydrofuran claim 1 , ethyl acetate claim 1 , 1 claim 1 ,2-dimethoxyethane claim 1 , dichloromethane claim 1 , 1 claim 1 ,4-dioxane claim 1 , toluene claim 1 , anisole claim 1 , ethanol claim 1 , acetone claim 1 , N claim 1 ,N-dimethylformamide claim 1 , N claim 1 ,N-dimethylacetamide claim 1 , pyridine and isopropyl acetate or a combination of two or more thereof.6. The process of claim 5 , wherein step (a) is carried out in a solvent selected from tetrahydrofuran and 1 claim 5 ,4-dioxane.7. The process of claim 1 , wherein in step (b) claim 1 , the base is sodium hydroxide claim 1 , potassium carbonate claim 1 , ammonium hydroxide claim 1 , potassium phosphate tribasic or sodium carbonate.8. The process of claim 7 , wherein the base is 1N sodium hydroxide claim 7 , 5 wt % potassium carbonate claim 7 , 28-30% ammonium hydroxide claim 7 , 10 wt % potassium phosphate tribasic or 5 wt % sodium carbonate.9. The process of claim 1 , wherein in step (a) the compound of Formula (I′) is in a mixture with its enantiomer.10. The process of claim 9 , wherein the mixture is a racemic mixture.13. The process of claim 11 , wherein X is N.14. The process of claim 11 , wherein X is CH.15. The process of claim 11 , wherein step (a) is carried out in a solvent selected from acetonitrile claim 11 , methanol claim 11 , tetrahydrofuran claim 11 , 2-methyltetrahydrofuran claim 11 , ethyl acetate claim 11 , 1 ...

Verfahren zur trennung verbindungsbildender chiraler systeme

Die Erfindung betrifft ein Verfahren zur Racemattrennung für verbindungsbildende Substanzen. Bei diesem Verfahren wird in einem Verfahrensschritt wenigstens eine mit einem Enantiomer angereicherte Fraktion erzeugt. Schließlich wird an der Fraktion eine bevorzugte Kristallisation durchgeführt.

Resolution of pure enantiomer of 1,1'-bi-2-naphthol

PURPOSE: Provided is a method for preparing the optical isomers of 1,1'-bi-2-naphthol to improve the purity and the yield, wherein the optical isomers is used as a chiral ligand for the asymmetric catalytic reaction. CONSTITUTION: The method comprises the steps of condensing the racemic mixture of 1,1'-bi-2-naphthol represented by the formula 1 with 2,2'-dimethylcyclopropanecarboxylic acid represented by the formula 2 to obtain the mixture (the formula 3) of (S)-1,1'-bi-2-naphthol-mono-2,2'-dimethylcyclopropanecarboxylate and (R)-1,1'-bi-2-naphthol-mono-2,2'-dimethylcyclopropanecarboxylate; recrystallizing the mixture (the formula 3) to separate (S)-1,1'-bi-2-naphthol-mono-2,2'-dimethylcyclopropanecarboxylate and (R)-1,1'-bi-2-naphthol-mono-2,2'-dimethylcyclopropanecarboxylate; and hydrolyzing the separated two isomers to obtain (S)-1,1'-bi-2-naphthol-mono-2,2'-dimethylcyclopropanecarboxylic acid and (R)-1,1'-bi-2-naphthol-mono-2,2'-dimethylcyclopropanecarboxylic acid. Preferably 2,2'-dimethylcyclopropanecarboxylic acid of the formula 2 is (S)-2,2'-dimethylcyclopropanecarboxylic acid. The recrystallization is carried out by using n-hexane.

Separation of diastereoisomers

Process for obtaining optically active phenylglycine

Method for optical resolution of racemic lysine sulfonate

Manufacturing Process of Optically Active [6-2-(Aminoethyl)-(4R,6R)-2,2-dimethyl-[1,3]dioxan-4-yl]acetic acid Derivative as Intermediate of Atorvastatin

본 발명은 3-히드록시-3-메틸글루타릴 조효소 (HMG-CoA)의 억제제인 아트로바스타틴(Atorvastatin)의 유용한 핵심 중간체로서 알려진 하기 화학식 4의 광학활성 [6-(2-아미노에틸)-(4R,6R)-2,2-디메틸-[1,3]디옥산-4-일]아세트산 유도체의 제조방법에 관한 것이다. 본 발명은 종래 출발물질인 알콜 화합물이 니트릴 화합물 또는 니트로 화합물로 변환시 두 단계를 거치고 초저온 반응을 필요로 하며 50 내지 70 % 정도의 낮은 수율을 보였던 것에 반해, 상온에서의 1 단계 반응으로 이루어지며 수율도 90 %로 매우 높다. 또한, 상기 니트릴 화합물 또는 니트로 화합물로부터 최종 화합물을 제조하는 종래 방법은 고압의 수소화 반응이나 폭발성의 환원제를 사용하는 단점이 있었으나, 본 발명은 취급이 용이하고 저렴한 반응물들을 사용함으로써 경제성 및 작업성 내지 안전성을 현저히 제고한 장점이 있다. The present invention relates to optically active [6- (2-aminoethyl)-of formula (4), which is known as a useful key intermediate of Atorvastatin, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme (HMG-CoA). A method for producing a (4R, 6R) -2,2-dimethyl- [1,3] dioxan-4-yl] acetic acid derivative. In the present invention, the alcohol compound, which is a conventional starting material, undergoes two steps when converted into a nitrile compound or a nitro compound, requires a cryogenic reaction, and shows a low yield of about 50 to 70%. It is also very high at 90%. In addition, the conventional method for preparing the final compound from the nitrile compound or nitro compound has the disadvantage of using a high-pressure hydrogenation reaction or an explosive reducing agent, the present invention is economical and workability to safety by using easy and inexpensive reactants It has the advantage of significantly improved. [화학식 4] [Formula 4] 상기 반응식에서 R 1 은 수소, 알킬, 또는 알킬아릴을 나타낸다. R 1 in the above scheme represents hydrogen, alkyl, or alkylaryl. 아트로바스타틴, 중간체 Atorvastatin, Intermediates

Crown Ether Chiral Statioary Phases and Chiral Columns for the Liquid Chromatographic Resolution of Chiral Drugs

본 발명은 광학활성 (18-크라운-6)-2,3,11,12-테트라카복시산을 LC 용 실리카 젤에 공유 결합시켜 합성된 키랄 고정상 및 이들로 충진된 키랄 칼럼을 개량하여 광학분할 성능을 향상시킨 키랄 고정상 및 이들로 충진된 키랄 칼럼의 제조에 관한 것이다. The present invention provides an optical splitting performance by improving a chiral stationary phase and a chiral column packed with optically active (18-crown-6) -2,3,11,12-tetracarboxylic acid covalently bonded to silica gel for LC. It is directed to the preparation of chiral stationary phases which have been improved and chiral columns filled with them. 즉, 본 발명은 광학활성인 (18-크라운-6)-2,3,11,12-테트라카복시산 [(2R,3R,11R,12R)-과, (2S,3S,11S,12S)-1,4,7,10,13,16-hexaoxacyclooctadecane- 2,3,11,12-tetracarboxylic acid] 의 무수물 중 선택된 어느 하나와, N-페닐아미노알킬 실리카 젤과, N-벤질아미노알킬 실리카 젤과, N-알킬아미노알킬 실리카 젤 중 선택된 어느 하나와 반응시킨 키랄 고정상(CSP 1)과, 이들 키랄 고정상(CSP 1)들로 충진된 LC 용 키랄 칼럼의 제조에 관한 것으로서, 일차 아미노기를 가지고 있는 키랄 의약품들을 제조하고 생산하는 과정에서 필수적으로 요구되는 광학활성 물질의 획득 및 광학활성 물질의 광학순도 측정 기술을 제공함에 요지가 있다. That is, the present invention provides optically active (18-crown-6) -2,3,11,12-tetracarboxylic acid [(2R, 3R, 11R, 12R)-and (2S, 3S, 11S, 12S)- 1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid], N-phenylaminoalkyl silica gel, N-benzylaminoalkyl silica gel, And a chiral stationary phase (CSP 1) reacted with any one selected from N-alkylaminoalkyl silica gel and a chiral column for LC filled with these chiral stationary phases (CSP 1). The present invention provides a technique for acquiring an optically active material and measuring optical purity of the optically active material, which are indispensable in the manufacture and production of medicines.

Preparation method of dexmedetomidine hydrochloride

本发明公开了一种盐酸右美托咪定的制备方法，包括以下步骤：在反应溶剂二氯甲烷中，1‑(1‑氯乙基)‑2,3‑二甲基苯与N‑TMS咪唑在路易斯酸四氯化钛作用下发生傅克反应生成美托咪定；在反应溶剂乙醇中，采用L‑(+)‑酒石酸对美托咪定进行拆分，得到右旋构型的美托咪定；在反应溶剂乙酸乙酯中，右美托咪定在盐酸溶液中成盐得到盐酸右美托咪定粗品，最后经过重结晶方式进行精制得到盐酸右美托咪定成品。该制备方法步骤少，操作简便且适合于工业生产。

Liquid Chromatographic Crown Ether Chiral Statioary Phases with Double Tethering Groups and Chiral Columns Packed with Them

본 발명은 광학활성인 (18-크라운-6)-2,3,11,12-테트라카복시산을 LC 용 실리카 젤에 공유 결합시켜 합성된 키랄 고정상 및 이들로 충진된 키랄 칼럼들의 수명이 제한적인 것을 개량하여 광학분할 성능을 그대로 유지한 채 그 수명을 향상시킨 키랄 고정상 및 이들로 충진된 키랄 칼럼의 제조에 관한 것이다. The present invention provides a limited lifetime of chiral stationary phases and chiral columns filled with the optically active (18-crown-6) -2,3,11,12-tetracarboxylic acid covalently bonded to silica gel for LC. The present invention relates to a chiral stationary phase and a chiral column filled with the same, which have been improved by improving the lifespan while maintaining optical splitting performance. 즉, 본 발명은 광학활성인 (18-크라운-6)-2,3,11,12-테트라카복시산 [(2R,3R,11R,12R)- 혹은 (2S,3S,11S,12S)-1,4,7,10,13,16-hexaoxacyclooctadecane- 2,3,11,12-tetracarboxylic acid]으로부터 합성된 광학활성인(18-크라운-6)-2,3,11,12-테트라카복시산 무수물을 이중 연결가지를 가지는 아미노디알킬실리카 젤과 반응시켜 제조된 화학식 1로 표현되는 키랄고정상들(CSP 1 및 CSP 2 )과, 상기 키랄고정상들(CSP 1 및 CSP 2 )로 충진된 LC 용 키랄 칼럼 혹은 HPLC 용 키랄 칼럼에 관한 것으로서, 단일 연결가지를 가지는 아미노알킬실리카 젤을 사용하여 제조된 키랄고정상들과 이들로 충진된 키랄칼럼의 수명을 획기적으로 증진시키는데 그 요지가 있다. That is, the present invention provides optically active (18-crown-6) -2,3,11,12-tetracarboxylic acid [(2R, 3R, 11R, 12R)-or (2S, 3S, 11S, 12S) -1 (4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid) optically active (18-crown-6) -2,3,11,12-tetracarboxylic anhydride And chiral stationary phases (CSP 1 and CSP 2 ) represented by Chemical Formula 1 prepared by reacting with an aminodialkylsilica gel having a double-linked branch, and chiral LCs filled with the chiral stationary phases (CSP 1 and CSP 2 ) The present invention relates to a column or a chiral column for HPLC, which is intended to drastically increase the lifespan of chiral stationary phases prepared using aminoalkylsilica gels having a single linking branch and chiral column filled with them.

Method for synthesizing medical intermediates

本发明公开了一种医药中间体R‑α‑环戊基（苯基）甲胺的合成方法，本发明的具体方法是；在催化剂的作用下苯基环戊酮还原胺化生成外消旋α‑环戊基（苯基）甲胺，α‑环戊基（苯基）甲胺再经脂肪酶与消旋催化剂结合进行动态动力学拆分得R‑α‑环戊基（苯基）甲胺。本发明具备操作简单、原料来源广、产品收率好、拆分产品光学纯度高等特点。

Liquid chromatographic chiral stationary phases and chiral columns for the resolution of racemic compounds containing primary amino group

PURPOSE: A LC chiral fixed phase is provided to effectively react in the optical resolution of racemic compounds such as medicines having primary amino group by covalent bonding optically activated compounds with silica gel. CONSTITUTION: The LC chiral fixed phase for efficiently reacting in the optical resolution of racemic compounds having primary amino group is produced by covalent bonding (18-crown-6)-2,3,11,12-tetracarboxylic anhydride or bispyridino-(18-crown-6)tetra carboxylic anhydride with the aminopropyl silica gel or mercapto-propyl silica gel. The tetracarboxylic anhydrides are prepared by reacting (18-crown-6)-2,3,11,12-tetracarboxylic acid ((2R,3R,11R,12R)-1,4,7,10,13,16-hexaoxacyclo octadecane-2,3,11,12-tetracarboxylic acid) of formula 1 or bispyridino-(18-crown-6)tetra carboxylic acid ((4R,5R,15R,16R)-3,6,-14,17-tetracarboxylic acid) of formula 2 with acetic anhydride. The chiral fixed phase is preferably CSP3 and CSP4 and forms the chiral column.

PRO

Patent FR2228745B1

OPTICALLY ACTIVE PHENYLGLYCINAMIDE PREPARATION PROCESS

A method for resolving optical isomers

The object of the present invent:ion is to provide a method for efficiently resolving optical isomers. The object of the present invention can be achieved by a method for resolving optical isomers, in which an discriminating liquid consisting of an discriminating agent capable of discriminating optical isomers and a diluent is brought into contact with a mixture containing said optical isomers in counter current, to resolve the optical isomers by adsorption separation, distillation separation, absorption separation or membrane separation, and is recovered at an optical isomer content of 5 wt% or less for recycled use, characterized by satisfying one or move of the following conditions (a) The dielectric constant of the diluent is 30 or less and the viscosity of the discriminating liquid is 0.2 Pa's or less at the temperature of the resolving operation. (b) The discriminating agent contained has an effect of splitting the 1H or 13C-NMR spectrum peak of the optical isomers when added and the diluent contained has a dielectric constant equal to or lower than the dielectric constant of the measuring solvent at the time of measuring the 1H or 13C-NMR spectrum. (c) The boiling point of at least one compound of the discriminating agent at the pressure of resolving operation is higher than the boiling point of at least one compound of the diluent at the pressure of resolving operation. (d) The boiling point of at least one compound of the diluent at the pressure of resolving operation is higher than the boiling point of the optical isomers to be resolved, at the pressure of resolving operation by 10°C or more. (e) The concentration of,the discriminating agent in the discriminating liquid is 10 wt% or more.

Sepn of stereoisomers - by extn and distn with an optically active solvent

PROCEDURE FOR THE OPTICAL RESOLUTION OF RACEMIC LYSINE SULFANILATE AND OPTICALLY ACTIVE PRODUCT SO OBTAINED

Crown Ether Chiral Stationary Phase and Chiral Column for the Liquid Chromatographic Resolution of Biologically Active Racemic Primary Amino Compounds

본 발명은 라세미 의약품들 중 아미노산, 아미노 알코올, 아민 등과 같이 일차 아미노기를 가지고 있는 라세미 생리활성 물질(라세미 의약품 포함)을 구성하는 두 개의 광학 이성질체를 분리하는데 아주 유용한 것으로 알려져 있는 새로운 크라운 에테르 키랄고정상을 개발하고 이것을 충진한 키랄 칼럼의 제조에 관한 것이다. The present invention is a new crown ether known to be very useful for separating two optical isomers which constitute racemic bioactive substances (including racemic drugs) having primary amino groups, such as amino acids, amino alcohols, amines, etc. It relates to the development of a chiral stationary phase and the preparation of a chiral column packed with it. 즉, 본 발명은 광학활성인 디페닐이 치환된 알파,알파-비나프틸-20-크라운-6(diphenyl substituted alpha,alpha'-binaphthyl-20-crown-6)( 1 )의 O-알킬화 반응(O-alkylation) 및 히드로실릴화 반응(hydrosilylation)에 의해 합성된 실릴(silyl) 화합물, 혹은 광학활성인 디페닐이 치환된 알파,알파-비나프틸-20-크라운-6( 1 )의 O-에스테르화 반응(O-esterification) 및 히드로실릴화 반응(hydrosilylation)에 의해 합성된 실릴 화합물 혹은 광학활성인 디페닐이 치환된 알파,알파-비나프틸-20-크라운-6( 1 )과 이소이아나토알킬트리에톡시실란(isocyanatoalkyltriethoxysilane) 화합물의 반응에 의해 합성된 실릴 화합물을 실리카 젤과 반응시켜 제조된 키랄고정상들 (CSP 2 ) 과 이들 키랄고정상들로 충진된 LC 혹은 HPLC 용 키랄칼럼을 득할 수 있는 것으로서, 일차 아미노기를 가지고 있는 라세미 의약품의 광학분할을 가장 효과적으로 할 수 있도록 하여 키랄의약품을 개발하고 생산하는 과정에서 반드시 필요한 광학순도 측정 기술을 제공함에 요지가 있다. That is, the present invention is an O-alkylation reaction of diphenyl substituted alpha, alpha'-binaphthyl-20-crown-6 ( 1 ) substituted with optically active diphenyl. O of an alpha, alpha-binafthyl-20-crown-6 ( 1 ) substituted with a silyl compound synthesized by (O-alkylation) and hydrosilylation, or an optically active diphenyl. Alpha, alpha-binafthyl-20-crown-6 ( 1 ) and isoi substituted with silyl compounds synthesized by O-esterification and hydrosilylation or with optically active diphenyl Chiral solid phases (CSP 2 ) prepared by reacting silyl compounds synthesized by the reaction of an anatocyanatoalkyltriethoxysilane compound with silica gel and chiral columns for LC or HPLC filled with these chiral solid phases are obtained. Optical division of racemic medicine which has primary amino group as possible The key point is to ...

Synthesis method of medetomidine

现有合成路线存在以下缺点：1、路线步骤多，原料价格昂贵，成本较高且难得到；2、整体路线过长、繁琐，降低产物的总产率，提高合成成本；3、使用危险剧毒的试剂，对设备要求较高，不利于大规模生产。本发明公开了一种美托咪定的合成方法，采用1‑三苯甲基咪唑‑4‑甲醛和2,3‑二甲基苯基溴化镁进行亲核加成反应，接着通过采用磷叶立德生成烯烃，然后加氢还原得到美托咪定。本发明还公开了一种盐酸右美托咪定的合成方法，将美托咪定拆分得到右美托咪定，然后将右美托咪定碱洗后，再加入盐酸生成盐酸右美托咪定。本发明简化合成路线，优化后处理方式，反应条件温和，污染小、易控制，所得产品的收率较高，纯度较好，可实现工业化生产。

METHOD FOR OPTICAL CLEAVAGE OF RACEMIC LYSINE SULFANILATE

RECOVERY OF OPTICAL ISOMERS AND SOLVENTS IN OPTICAL RESOLUTION, REUSE OF THE SOLVENT AND OPTICAL ISOMERS AFTER RECYCLING

Process for separating optical isomers

Patent FR2228745A1

METHOD FOR OPTICAL CLEAVAGE OF RACEMIC LYSINE SULFANILATE

Optically-active, amphiphilic, water-soluble free-radical addition copolymers and their use in the resolution of racemic mixtures

METHOD FOR DEDOLDING ENANTIOMERS BY PREFERENTIAL EVAPOCRYSTALLIZATION

La présente invention concerne un procédé de dédoublement de deux énantiomères, consistant à induire la cristallisation préférentielle d'un énantiomère en ajustant la composition d'une suspension ou solution renfermant un mélange racémique des deux énantiomères et un solvant, par évaporation de ce dernier. The present invention relates to a method for resolving two enantiomers, comprising inducing the preferential crystallization of an enantiomer by adjusting the composition of a suspension or solution containing a racemic mixture of the two enantiomers and a solvent, by evaporation of the latter.

Methods for the separation of modafinil

The present invention is directed to a process for the isolation of the enantiomeric forms of modafinil with high enantiomeric purity and high overall yields by means of a continuous chromatographic process.

Resolution of racemic reticuline and racemization of its enantiomers

Racemic reticuline is resolved by forming a crystalline diastereomeric acid salt with a mandelic acid enantiomer. The reticuline enantiomers are racemized by treatment with a reduced noble metal or noble metal oxide catalyst. (-)-Reticuline is a valuable intermediate useful in the synthesis of thebaine, and (+)-reticuline is useful as a precursor of pallidine, sinoacutine, coreximine, and the berberine alkaloids.

PROCESS FOR PREPARATION OF OPTICALLY ACTIVE PHENYLGLYCINEAMIDE.

Separation of diastereomers

The S,S-isomers of Boc-benztine and Boc-cyclotine can be produced via the fractional crystallization of R-(+)-alpha-methylbenzylamine salt(s). The products are useful in the production of renin inhibitors.

Optical resolution of DL-α-phenylglycine hydrochloride

In order to separate optically active D- or L-α-phenylglycine hydrochloride from a supersaturated solution of DL-α-phenylglycine hydrochloride seed crystals of the desired D- or L-isomer are added to the solution in the presence of a metal chloride.

Chemical process

Process for racemisation of amino acids by use of a ketone and an organic acid such as acetic acid. In particular, a process for resolution of free a-amino acdis with in situ racemisation. The resolution of 4 hydroxyphenylglycine and 3,4 dihydroxyphenylglycine with 3-bromocamphor-9-sulphonic acid with in situ racemisation are specifically mentioned.

Amino-acid resolution

1427785 Levo-erythro-ethenamine D-(-)-2- acetylamino - 2 - 4 - (acetoxyphenyl)acetate; amino-acid resolution BRISTOL-MYERS CO 14 Sept 1973 [15 Sept 1972] 43232/73 Head- C2C The invention comprises the compound (I) levo - erythro - ephenamine - D - (-) - 2 - acetylamino - 2 - (4 - acetoxyphenyl) acetate. It may be prepared by reacting racemic 2-acetylamino-2-(4-acetoxyphenyl)acetic acid with levoerythro-ephenamine by dissolving the reactants in a suitable solvent and recovering the desired compound from solution. The compound may be reacted with a strong base to give the free base levo-erythro-ephenamine and D- (-) - N - acetyl - 2 - (4 - acetoxyphenyl) - glycine which may be reacted with a strong acid to give the corresponding acid addition salt of D- (-)- 2 - amino - 2 - (4 - hydroxy - phenyl)acetic acid which can be converted to the free acid by treatment with an alkali. Racemic 2-amino-2-(4- hydroxyphenyl)acetic acid may be resolved into its levo-rotatory isomer by acetylating the racemic acid to form racemic 2-acetylamino-2- (4-acetoxyphenyl) acetic acid, reacting the acetylated acid with levo-erythro-ephenamine solution, recovering the compound of Formula (I) above, reacting this with a strong base, removing the levo-erythro-ephenamine released, reacting the residual D-(-)-N-acetyl-2-(4-acetoxyphenol)glycine with a strong acid to provide the corresponding addition salt of D-(-)-2- amino - 2 - (4 - hydroxyphenyl)acetic acid and treating this in an alkaline medium to release the desired levo-rotatory isomer.

Chiral recognition polymer and its use to separate enantiomers

A new polymeric material, a process for forming the material and method of using the material to separate enantiomers of chiral compounds, particularly amino acids and pharmaceuticals are disclosed. A polymeric material can be formed from polyaniline doped with a chiral acid and then extracted with a suitable base. This leaves behind a polymeric material which preferentially traps, and then selectively releases, one enantiomer of a chiral mixture brought in contact with the surface of the polymeric material. In particular, when polyaniline is doped with either R- or S-camphorsulfonic acid (CSA) it takes on a chiral structure. Removing the chiral acid dopant leads to a new chiral polyaniline. The dedoped chiral polyanilines have the ability to discriminate among enantiomers of many compounds which exist in chiral mixtures.

Chemical process

(57)【要約】本公報は電子出願前の出願データであるた め要約のデータは記録されません。

Patent FR2200249B1

Patent FR2305412B1

Process for optical purification of d-p-hydroxyphenyl-glycine

1476110 Obtaining optically pure D-p-hydroxyphenylglycine PFIZER Inc 20 Nov 1975 [9 Jan 1975] 47870/75 Heading C2C The invention comprises a process for separating D-p-hydroxyphenylglycine from a mixture containing D and DL-p-hydroxyphenylglycine and/or the C 1-10 alkyl esters thereof wherein (a) said mixture is dissolved in aqueous hydrobromic acid (b) insoluble DL-p-hydroxyphenylglycine HBr is separated from the solution, (c) the pH of the solution is adjusted to a value in the range 4À0 to 6À0 and (d) isolating the D- isomer from the solution in crystalline form. The hydrobromide of D-p-hydroxyphenylglycine may be isolated from stage (b) after separation of the DL isomer by, e.g. evaporation of the HBr and then dissolved to form an aqueous solution from which the free amino acid can be obtained by treatment with alkali. When the starting material is or includes C 1-10 alkyl esters these are hydrolysed during the reaction.

Method for separating compound-forming chiral systems

Methods for racemate separation for compound-forming substances. In this method, at least one fraction which is enriched with an enantiomer is produced in one method step. Finally, a preferred crystallization is carried out on the fraction.

Method for recovering optical isomer and solvent in optical resolution, method for recycling solvent, and method for reusing optical isomer

Chemical process

Process for obtaining pure optically active homocysteic acid

METHOD FOR DEDOLDING ENANTIOMERS BY PREFERENTIAL EVAPOCRYSTALLIZATION

Alpha-azido-phenyl-acetic acid optical isomer sepn - by forming diastereo-isomeric salts with alpha-phenyl-ethylamine

Process comprises sepg. D (-) and L (+) optical isomers of alpha-azidophenylasetic acid (I) by reacting racemic (I) in polar solvent with one of the optical isomers of alpha-phenylethylamine (II), crystallizing and sepg. the diastereo isomeric salts, with the improvement tht 0.1-0.5 moles of L(-) or D(+) (II) are used per mole DL (I). This gives higher yield and purer product than prior art use of equimolar amts. of (I) and (II). D(-) (I) is a starting matl. for antibiotics such as alpha-aminobenzyl- and alpha-azidobenzyl-penicillins.

PROCEDURE FOR SEPARATING DIASTEREOMERS.

Patent FR2200249A1

Resolution method for preparing l-muscone stereoselectively

본 발명은 3-메칠 시클로펜타데칸-1-온(Ⅱ)에 트레이톨 유도체들을 반응하여 dl -무스콘 케탈 화합물(Ⅲ)을 만든 후 이를 가수분해하여 l -무스콘(I)을 분리 정제하는 방법에 있어서, 순상 크로마토그래피 조건 하에서 dl -무스콘 케탈 화합물(Ⅲ)을 분취한 후 이를 가수분해하여 입체선택적으로 l -무스콘(I)을 분리 정제하는 방법을 제공하는 것이다. In the present invention, dl -muscon ketal compound (III) is made by reacting pentitol derivatives with 3-methylcyclopentadecan-1-one (II), and then hydrolyzed to separate l -muscon (I). In the method, a dl -muscon ketal compound (III) is collected under normal phase chromatography conditions and then hydrolyzed to provide a method for stereoselectively separating l -muscon (I). (반응식 1) (Scheme 1) 상기식에서 R 1 은 아래 구조식의 관능기를 나타낸다. In formula, R < 1> represents the functional group of the following structural formula.

Coherently controlled laser distillation of chiral enantiomers

A laser-based method of enhancing the enantiomeric excess of one chiral enantiomer in a mixture of chiral enantiomers, denoted L and D (and related to one another by the inversion operation I), is described. The molecule L and D is chosen so that electronic excitation is to an electronically excited species with stationary ro-vibrational states which are individually either symmetric or anit-symmetric with respect to I. The mixture is irradiated with a series of achiral pulses of coherent laser light. By varying the frequencies, timing, and durations of these pulses one can selectively increase the enantiomeric excess of either L or D in the ground electronic state.

Process for the preparation of optically active α-phenylglycine and intermediates thereof

DL- α-phenylglycine can be combined with benzene-sulfonic acid, p-ethylbenzenesulfonic acid or m-xylenesulfonic acid to give the salt. The salt of the racemate may be more soluble in a sulfuric acid solution than the salt of the optically active isomer by suitably choosing the concentration of the sulfuric acid solution, and then the optical resolution by fractional crystallization is carried out. The D- or L- α-phenylglycine sulfonate is easily liberated of the sulfonic acid portion to give optically active D- or L- α-phenylglycine.

A kind of method for preparing dexmedetomidine hydrochloride

本发明涉及到一种制备盐酸右美托咪定的方法。所述方法具体包括如下步骤：1)将消旋体美托咪定溶于甲醇后与右旋拆分剂按摩尔比1:0.4‑0.6混合，在60‑80℃加热条件下搅拌2‑3个小时，加入乙醚冷却静置析晶，过滤，母液与左旋拆分剂按摩尔比1:0.4‑0.6的比例混合，搅拌析晶24小时，过滤得到右旋美托咪定；2)所得右美托咪定在HCl/乙醚中形成最终产物盐酸右美托咪定。与现有技术相比，本发明降低成本地制备盐酸右美托咪定；合成路线短，可制备高纯度的盐酸右美托咪定，并且异构体未检出，质量达到药典最新标准，有利于工业化生产；所用原材料成本较低，反应条件温和，可应用于实际生产。

Optical resolution of dl-alanine maleate

1345113 Alanine monomaleates; resolutions thereof; resolving DL-alanine AJINOMOTO CO Inc 16 March 1972 12447/72 Heading C2C The invention comprises DL-, D- and L- alanine monomaleates; and a process for resolving DL-alanine monomaleate by contacting a supersaturated solution thereof with seed crystals of one or both enantiomorphs; in the latter case the seed crystals and grown crystals are separate or separable from one another. Various embodiments are described. The resulting D- or L-alanine monomaleate can be treated (i) with sodium hydroxide and/or disodium maleate to precipitate monosodium maleate; (ii) with calcium hydroxide and/or monocalcium maleate to precipitate hemi and/or monocalcium maleate; (iii) with barium hydroxide to precipitate monobarium maleate; in each case recovering D- or L-alanine; details of these procedures being given.

Patent FR2239438A1

PROCEDURE FOR THE INSULATION OF THE OPTICAL ANTIPODS OF HAND ACID AND MORE ALPHA AZIDOFENILACETICO

Process for producing salt of l-isomers of phenyl-glycine derivatives

Resolution method of racemic mixture

S P E C I F I C A T I O N Abstract of the Disclosure A novel resolution method of a racemic mixture, wherein four kinds of salts are dissolved in a resolving solvent to fractionally crystallize a dessired optically active isomer through an exchange reaction between counter ions.

Optically active 1,1'-biphenanthryl-2,2'-diol, process for preparing the same, and resolving reagent comprising the same

The novel optically active 1,1'-biphenanthryl-2,2'-diol is disclosed, which is obtained by preparing N((S)-1-phenylethyl)-1,1'-biphenanthryl-2,2'-diylthiophosphorylamide by using optically active phenylethylamine, recrystallizing the compound into an optically active compound, followed by reduction with a reducing agent. The diol compound according to the present invention is useful as a resolving reagent, a starting material of an optically active phosphine compound or a ligand in asymmetric synthesis, forming a complex with a transition metal or a rare earth element to provide a useful catalyst.

Method for the optical resolution of racemic homocysteic acid or its monoammonic salt

Methods for Separating Modafinil

Separation of diastereomers

The S,S-isomers of Boc-benztine and Boc-cyclotine can be produced via the fractional crystallization of R-(+)-alpha-methylbenzylamine salt(s). The products are useful in the production of renin inhibitors.

Separazione di aminoacidi in antipodi ottici.

Optically active 3-hydroxy-n-methyl-morphinanes and process for the manufacture thereof

The optical isomers of 3-hydroxy-N-methylmorphinane are prepared by resolving 1-(p-methoxybenzyl)-2-methyl-1 : 2 : 3 : 4 : 5 : 6 : 7 : 8-octahydroisoquinoline by means of an optically active acid and cyclising the optical antipodes separately. The latter may be isolated as tartrates which are subsequently converted into the free bases. Resolution of the isoquinoline may be effected by fractional crystallization of the tartrate from water or methanol or a mixture of the two. The tartrate which crystallizes first is laevorotatory in ether and (after conversion to the free base) gives the d-(+)-morphinane on cyclizing with phosphoric acid. From the mother liquor is obtained the tartrate which is dextrorotatory in ether and this can be converted into free base and cyclised to the l-(-)-morphinane. Alternatively the crude mother liquor can be cyclised directly and resolution completed at the morphinane stage. The process is exemplified.

Process for production of optically active amines

Verfahren zur abtrennung von modafinil

리파아제를 이용한 아지리딘-2-카르복시산 에스테르의입체선택적 가수분해 방법

본 발명은 아지리딘-2-카르복시산 에스테르로부터 리파아제를 이용한 광학분리를 통하여 광학활성의 가수분해산물인 아지리딘-2-카르복시산 유도체 및 반응하지 않고 남아 있는 광학활성 산물인 아지리딘-2-카르복시산 에스테르를 각각 수득하는 방법에 관한 것이다. 본 발명은 상기 구조식 (1)의 라세믹 혼합물 또는 부분입체이성질체 혼합물인 아지리딘-2-카르복시산 에스테르를 아민으로 포화된 알코올 용매에서 리파아제를 이용하여 가수분해시켜 구조식 (2)의 광학활성 가수분해 산물인 아지리딘-2-카르복시산 아미드 및 반응하지 않고 남아 있는 구조식 (3)의 광학활성 산물인 아지리딘-2-카르복시산 에스테르를 각각 수득하는 방법에 관한 것이며 R 1 은 벤질, (R)-페닐에틸, 또는 (S)-페닐에틸이고, R 2 는 메틸, 에틸, n-부틸을 포함한다.

Racemisation of optically active naphthalene derivatives

Optically active compounds of the general formula <FORM:1024914/C2/1> (wherein R1 stands for a hydrogen atom or methyl radical, R2 stands for an alkyl radical, optionally substituted by one or more substituents selected from hydroxy, alkoxy, phenyl, alkoxyphenyl, dialkoxyphenyl, trialkoxyphenyl and alkylphenyl radicals, and the naphthalene nucleus may optionally bear one or more halogen or hydroxy substituents or alkyl or alkoxy radicals of not more than six carbon atoms) are racemized by heating with an inorganic or organic acid.

Verfahren zur trennung optischer isomere

Optisch aktive 1,1'-Biphenanthryl-2,2'-diol, Verfahren zu ihrer Herstellung, und diese enthaltendes Mittel zur optischen Spaltung

Optisch aktive 1,1'-Biphenanthryl-2,2'-diol, Verfahren zu ihrer Herstellung, und diese enthaltendes Mittel zur optischen Spaltung

光学活性なエトドラクの製造方法

　本発明は、光学活性なエトドラクを製造するための新規な製法に関するものである。 　本発明の主目的は、生産性が高く、低コストで、しかも簡便に光学活性なエトドラクを製造することができる方法を提供することにある。 　本発明として、エトドラク、シンコニン及びメタノールを混合し懸濁状態とし、該懸濁物を静置又は攪拌することにより、（＋）－エトドラクとシンコニンとの塩を析出させ、かかる析出した塩から、又はかかる析出した塩を濾別することにより得られる濾液から（＋）－エトドラク又は（－）－エトドラクを得ることを特徴とする、光学活性なエトドラクの製造方法を挙げることができる。

［４−（２−ジフェニルホスファニルナフタレン−１−イル）フタラジン−１−イル］−（１−フェニルエチル）アミンの光学活性体の製造方法

【課題】カラムクロマトグラフィーによる分離を行うことなく簡便な方法によりＮ−ＰＩＮＡＰの光学活性体を提供する。 【解決手段】（Ｒ）−または（Ｓ）−［４−（２−ジフェニルホスファニルナフタレン−１−イル）フタラジン−１−イル］−（１−フェニルエチル）アミンの混合物の溶液と、光学活性な有機スルホン酸とを混合して晶析させる、（Ｒ，Ｐ）−［４−（２−ジフェニルホスファニルナフタレン−１−イル）フタラジン−１−イル］−（１−フェニルエチル）アミンの光学活性な有機スルホン酸塩または（Ｓ，Ｍ）−［４−（２−ジフェニルホスファニルナフタレン−１−イル）フタラジン−１−イル］−（１−フェニルエチル）アミンの光学活性な有機スルホン酸塩の製造方法。 【選択図】なし

用于制备光学活性胺的方法

本发明提供由式(1)至(4)表示的光学活性[4-(2-二苯基膦基萘-1-基)-2，3-二氮杂萘-1-基]-(1-苯基乙基)胺的光学活性有机磺酸盐及其制备方法。

用于制备光学活性胺的方法

本发明提供由式(1)至(4)表示的光学活性[4-(2-二苯基膦基萘-1-基)-2，3-二氮杂萘-1-基]-(1-苯基乙基)胺的光学活性有机磺酸盐及其制备方法。

광학 활성인 아민의 제조 방법

본 발명은 하기 화학식 (1) 내지 (4)로 표시되는 광학 활성인 [4-(2-디페닐포스파닐나프탈렌-1-일)프탈라진-1-일]-(1-페닐에틸)아민의 광학활성인 유기 술폰산 염 및 그의 제조 방법에 관한 것이다.

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Separation of chiral compounds

A method of separating the enantiomers of a chiral compound from a mixture, the mixture including a first and second enantiomer, by introducing the mixture into a fluid flow leading to a separation means which changes the distribution of the enantiomer concentrations so that the fluid flow includes at least a first region which includes the first enantiomer but substantially none of the second enantiomer and a second region which includes the second enantiomer but substantially none of the first enantiomer. A sensor means senses the mixture to produce a first sensor signal proportional to the sum of the concentration of the first enantiomer and the concentration of the second enantiomer, and a second sensor signal proportional to the difference between the concentration of the first enantiomer and the concentration of the second enantiomer. The first and second sensor signals are processed to detect the region in the fluid flow which includes the first enantiomer but substantially none of the second enantiomer and calculate its location, directing at least part of said region in the fluid flow which includes the first enantiomer but substantially none of the second enantiomer to a collecting means, leaving a remaining portion in the fluid flow.

Process for the preparation of isomeric racemic dihydro-nor-iysergic acids

The invention comprises racemic dihydronor-lysergic acid and the corresponding-isolysergic acids I and II. These are made by treating a compound of the formula <FORM:0676281/IV (b)/1> (R=alkyl) with a light metal and acid (e.g. zinc and hydrochloric) to give <FORM:0676281/IV (b)/2> and reducing the latter with sodium and an alcohol (e.g. butanol). The isomers produced can be separated by fractional crystallization or chromatography, preferably in the form of esters. In the latter case re-esterification of the product is necessary as the group R is split off during the second reduction step (or sometimes during the first). An example is given of the production of the three isomeric acids and their methyl esters, the acids being regenerated from the latter after purification.

Verfahren zur Trennung von optischen Antipoden

Improved process for synthesis of benazepril intermediate

The present invention relates to an improved process for the preparation for the stereo-specific preparation of Benazepril intermediate (3S)-3-[[(1S)-1- phenylethyl]amino]-1,3,4,5-tetrahydro-1-benzazepin-2-one of formula (IS). The steps include: heating the compound of Formula (I) (3RS)-[[(1S)-1-phenylethyl]amino]- 1,3,4,5-tetrahydro-1-benzazepin-2-one at a predefined temperature in a predefined solvent followed by separating undissolved desired isomer of formula (IS) from the reaction mixture of step (i); recovering the R-isomer of formula (IR) from the filtrate followed by distilling the filtrate to isolate the compound of R-isomer of formula (IR); racemizing R-isomer of formula (IR) to form racemic mixture of formula (I) and recovering the racemic compound obtained in step (iv) by distilling the solvent of previous step under vacuum and recycling by adding the racemic compound to step (i).

키랄 아미노산 검출용 조성물, 및 이를 이용한 아미노산의 키랄성 검출 방법

본원은 키랄 아미노산 검출용 조성물, 및 이를 이용한 아미노산의 키랄성 검출 방법을 제공한다.

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分离旋光异构体的方法

能旋光解析那些不能在常规的反相条件下旋光拆分的化合物的分离旋光异构体的方法。具体地说,通过用含多糖衍生物作为有效成分的分离剂的液相色谱分离旋光异构体的方法,其特征为在反相条件下用碱性流动相。

光学異性体分離法

(57)【要約】 【課題】 従来の逆相条件では、十分に光学分割できな かった化合物を光学分割可能とする光学異性体分離法の 提供。 【解決手段】 多糖誘導体を有効成分とする分離剤を用 いた液体クロマトグラフィーによる光学異性体の分離に おいて、逆相条件下で塩基性移動相を用いることを特徴 とする光学異性体分離法。

광학이성체 분리법

본 발명은 종래의 역상(逆相) 조건으로는 충분히 광학분할 할 수 없었던 화합물을 광학분할 가능하게 하는 광학이성체 분리법을 제공한다. 또, 본 발명은 다당유도체를 유효성분으로 하는 분리제를 사용한 액체 크로마토그래피에 의한 광학이성체의 분리에 있어서 역상조건하에서 염기성 이동상을 사용하는 것을 특징으로 하는 광학이성체 분리법을 제공한다.

Procede permettant de separer des isomeres optiques

Procédé de résolution optique des formes racémiques de l'acide glutamique et de ses dérivés

Trennung von optischen Isomeren

Procede de dedoublement de la dl-2-(4-hydroxyphenyl) glycine et nouveaux produits ainsi obtenus

Verfahren zur Herstellung von Salzen der l-Form des Isopropylaminomethyl-3,4-dioxyphenyl-carbinols

Werkwijze voor het scheiden van d1-2-amino-1- -butanol in de optische isomeren.

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Framstellning av d- och l-2-amino-1-butanol.

An industrial process for resolution of chlocyphos

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1,266,723. Resolution of racemates. AMERICAN CYANAMID CO. 25 July, 1969 [20 Aug., 1968; 20 May, 1969], No. 37487/69. Headings C2C and C2U. The resolution of a racemic alcohol is effected by (i) reacting it with an optically inactive amine-sulphur trioxide complex to form a racemic hemisulphate amine salt, (ii) treating the latter with an excess of an optically active primary amine to form a mixture of diastereomeric hemisulphate salts with said optically active amine, (iii) separating these salts by fractional crystallization and (iv) hydrolysing the separated salts to respective d and l alcohols. Specified racemic alcohols are dl-3-methoxy- 13# - ethyl - gona - 1,3,5(10) - trien - 17# - ol, dl - 3 - methoxy - 13# - ethylgona - 1,3,5(10),8- tetraen-17#-ol, dl-chloramphenicol and dl-pantothenic acid. Specified optically inactive amines are triethylamine and pyridine. Specified optically active primary amines are d- and l-2- aminobutanol, α-phenylethylamine and menthylamine. The resolution of a racemic ketone is effected by (i) reacting it with an optically active primary amine, preferably with acid catalysis, to form a mixture of diasteromeric imines which is then optionally salified (e.g. with HCl), (ii) separating the mixture of imines or imine salts by fractional crystallization, and (iii) hydrolysing the separated products to the respective d and l ketones. Specified racemic ketones are dlestrone, dl-androstenolone, dl-pregnenolone, dl- 3 - methoxy - 13# - ethylgona - 1,3,5(10) - trien- 17 - one and dl - 3 - methoxy - 13# - ethylgona- 1,3,5(10),8-tetraen-17-one. Specified optically active primary amines are d- and 1-2-aminobutanol, α-phenylethylamine and menthylamine. Compounds claimed per se are (i) d-3-methoxy - 17# - sulphoxy - 13# - ethylgona - 1,3,5- (10) - triene l - 2 - aminobutanol salt; and (ii) d- and l-3-methoxy-17-(l-1-ethyl-2-hydroxy. ethylimino) - 13# - ethylgona - 1,3,5(10) - triene and the hydrochlorides thereof.

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Verfahren zur Trennung von racemischen Alkoholen und Ketonen in die d- und l-Form