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Abstract

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Paper | Special issue | Vol 84, No. 1, 2012, pp. 577 - 585
Published online: 10th June, 2011
DOI: 10.3987/COM-11-S(P)23
Regioselective α-Monochlorination of N-Protected-3-piperidones

Pradeep S. Chauhan, Max M. Majireck, and Steven M. Weinreb*

*Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, U.S.A.

Abstract

A direct procedure for regioselective α-monochlorination of various N-sulfonyl and N-acyl-protected-3-piperidones with N-chlorosuccinimide (NCS) and Amberlyst-15 ion exchange resin is reported which leads predominantly (or exclusively) to 4-chloro-3-piperidones in all cases.

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