Process for preparing cis or trans, optically active monoalkyl e

Details Process for preparing cis or trans, optically active monoalkyl e Process for preparing cis or trans, optically active monoalkyl e

1983-07-06

1984-12-11

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

C07C 6974

Patent

active

044879555

ABSTRACT:
A novel process for the preparation of esters of 2,2-dimethyl-cyclopropane-1,3-dicarboxylic acids in their optically active forms having a cis or trans configuration I comprising salifying the monomethyl ester of (1RS,3SR) cis 2,2-dimethyl-cyclopropane-1,3-dicarboxylic acid with d or l .alpha.-methyl-benzylamine, recovering the crystallized salt formed, dissolving the said salt in water, treating the solution with a mineral base and then with an acid to obtain either the monomethyl ester of (1R,3S) cis 2,2-dimethyl-cyclopropane-1,3-dicarboxylic acid I or its (1S,3R) cis isomer depending on whether d or l .alpha.-methyl-benzylamine, respectively was used, if desired, reacting the latter cis compound with a strong base to isomerize the monomethyl ester to the monomethyl ester of (1S,3S) trans 2,2-dimethyl-cyclopropane-1,3-dicarboxylic acid I or (1R,3R) trans isomer, respectively, or reacting the latter cis compound with a tert-butyl esterification agent to obtain a compound of (1S,3R) configuration of the formula ##STR1## or a compound of (1R,3S) configuration of the formula ##STR2## subjecting the said compound to selective hydrolysis to remove the methyl ester group to form a compound of the formula ##STR3## of (1S,3R) cis or (1R,3S) cis configuration, respectively and optionally subjecting the compound of formula I.sub.A to a strong isomerization base to obtain a compound of the formula ##STR4## of (1R,3R) trans or (1S,3S) trans configuration which is a useful intermediate for the preparation of pesticidal compositions.

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