Optically active proline derivative, process for its production

Details Optically active proline derivative, process for its production Optically active proline derivative, process for its production

1982-09-28

1984-09-04

Brust, Joseph Paul

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

210656, 2101982, 548201, 548535, 562402, C07C20700, C07C20712, B01D 1508

Patent

active

044698755

ABSTRACT:
The invention is directed to optically active proline derivative of the general formula: ##STR1## 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 ##STR2## 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.

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Iskandarani, et al., Analytical Chemistry, 53 (3), Mar. 1981, pp. 489-495.
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C.A., 95: 23008j, (1981); Moll, et al.
Noller, Chemistry of Carbon Compounds, 3rd Ed., (1965), pp. 813-814, W. B. Saunders Co., Phila., Penna., U.S.A.
Lindner; Chimia, vol. 82, pp. 294-307, (1981).
Davankov, et al., Chromatographia, vol. 13, pp. 677-685, (1980).

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