Optically active proline derivative, process for its production and use

• Main Authors: MARTENS; JUERGEN, WEIGEL; HORST, STEIGERWALD; REGINA, BUSKER; EBERHARD
• Format: Patent
• Language: English
• Published: 04.09.1984
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIRCHEMICAL OR PHYSICAL PROPERTIES; MEASURING; METALLURGY; MIXING, e.g. DISSOLVING, EMULSIFYING, DISPERSING; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; PHYSICS; SEPARATION; TESTING; THEIR RELEVANT APPARATUS; TRANSPORTING

The invention is directed to optically active proline derivative of the general formula: (I) in which X is a hydrogen atom or a hydroxyl group and R is a hydrogen atom, an unsubstituted or alkyl group substituted phenyl group or a straight chain or branched alkyl group having 1 to 20 carbon atoms and a process for its production by reacting an enantiomerically pure proline or 4-hydroxy-proline as a solution in an alkanol having 1 to 4 carbon atoms with 0.9 to 2 times the molar amount of an alkali metal alcoholate corresponding to the alkanol and 1 to 3 times the molar amount of an epoxide of the general formula (II) in which R is as defined above. The optically active proline derivative of general formula (I) can be used in the form of metal ion chelate complexes as the chiral stationary phase in the separation of enantiomers by means of liquid chromatography.