Synlett 2006(11): 1679-1682  
DOI: 10.1055/s-2006-944214
LETTER
© Georg Thieme Verlag Stuttgart · New York

Anodic Cyanation of (S)-(-)-1-(1-Phenylethyl)piperidine: an Expeditious Synthesis of (S)-(+)-Coniine

Nicolas Girard, Laurent Pouchain, Jean-Pierre Hurvois*, Claude Moinet
Laboratoire d’Electrochimie et Catalyse, UMR 6226, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France
Fax: +33(2)23235967; e-Mail: Jean-Pierre.Hurvois@univ-rennes1.fr;
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Publikationsverlauf

Received 28 March 2006
Publikationsdatum:
04. Juli 2006 (online)

Abstract

A short and efficient asymmetric synthesis of enantiopure (S)-(+)-coniine is reported. Anodic cyanation of (-)-1-[(1S)-1-phenylethyl]piperidine, derived from [(1S)-1-phenylethyl]amine, results in regioselective formation of the corresponding α-amino­nitrile, which was alkylated with propyl iodide to give a bifunc­tional derivative. The latter underwent a stereoselective reductive decyanation (80% de), the product of which was hydrogenolyzed to afforded (S)-(+)-coniine (99% ee) with an overall 35% yield from (-)-1-[(1S)-1-phenylethyl]piperidine.

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Aminonitrile 3 readily decomposed on TLC plate, R f value is given for guidance.