Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters

Details Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters

1998-04-16

2000-02-22

Keys, Rosalynd

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

Organic compounds

Carboxylic acid esters

C07C 6974

Patent

active

060282134

ABSTRACT:
Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters of >90% enantiomeric excess (ee) and methods of preparing the monoesters are described. One method contacts a cis-1,3-cyclohexanedicarboxylic acid diester with a lipase under aqueous conditions to enantioselectively produce the optically active cis-1,3-cyclohexanedicarboxylic acid monoester. Another method reacts a mixture of cis- and trans-1,3-cyclohexanedicarboxylic acids under conditions sufficient to form a cis-cyclic anhydride, esterifies the cis-cyclic anhydride to produce a cis-1,3-cyclohexanedicarboxylic acid diester and then contacts under aqueous conditions the diester with a lipase to enantioselectively produce the optically active cis-1,3-cyclohexanedicarboxylic acid monoester.

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