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Paper | Regular issue | Vol 36, No. 8, 1993, pp.1791-1794
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6356
(S)-1,3-Dimethyl-3-hydroxy-5-methoxyoxindole: By-Product in the Synthesis of Physostigmine

Qian-sheng Yu, Yi-qun Li, Wei-ming Luo, and Arnold Brossi*

*Department of Chemistry, Georgetown University, Washington DC 20057, and Scientist Emeritus NIH, U.S.A.

Abstract

(S)-1,3-Dimethyl-3-hydroxy-5-methoxyoxindole (4) was obtained as a by-product in the asymmetric alkylation of oxindole (1) with methyl chloroacetate in the presence of N-[(4-trifluoromethyl)benzyl]cinchonium bromide. Its structure was established by spectral data. Optically active (4) of (S)-configuration was obtained from oxindole (1) on air oxidation in the presence of the chiral catalyst N-[(4-trifluoromethyl)benzyl]cinchonium bromide.