ChemInform Abstract: Facile Preparation of (3S)-1,3-Dimethyl-3-cyanomethyl-5-ethoxyoxindole from Julian′s Nitrile Enriched in the (3S)-Enantiomer.
Abstract
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ChemInform Abstract
The chiral phase transfer catalyzed asym. 3-cyanomethylation of 1,3- dimethyl-5-ethoxyoxindole (I) in the presence of a chiral catalyst provides the corresponding (S) enantiomer (III) with moderate e.e.; however, optical purification is easily achieved by recrystallization from isopropanol. Optically pure (III) is a key intermediate for the synthesis of physostigmine and related compounds, useful for the treatment of Alzheimer′s disease.
