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Paper | Regular issue | Vol 60, No. 7, 2003, pp.1601-1610
Published online, 19th May, 2003
DOI: 10.3987/COM-03-9784
A Facile and Practical Procedure for the Stereoselective Synthesis of (Z)-3-Quinuclidinylideneacetic Acid Derivative

Tsukasa Ishihara,* Shuichi Sakamoto, Shin-ichi Tsukamoto, and Isao Yanagisawa

*Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21, Miyukigaoka, Tsukuba, Ibaraki 305-8585, Japan

Abstract

A study of the isomerization of methyl (E)-3-quinuclidinylideneacetate derivative to the corresponding Z-isomer is reported. Theoretical calculations, performed using the MM3 molecular mechanics method, are in agreement with the experimental results. A facile and practical procedure for the stereoselective synthesis of methyl (Z)-3-quinuclidinylideneacetate derivative, via the Horner-Wadsworth-Emmons reaction with sodium methoxide in methanol, is also described.