Chlorination/Cyclodehydration of Amino Alcohols with SOCl₂: An Old Reaction Revisited

Feng Xu,* Bryon Simmons, Robert A. Reamer, Edward Corley, Jerry Murry and David Tschaen

*Department of Process Research, Merck Research Laboratory, Rahway, New Jersey 07065, Email: feng_xumerck.com

F. Xu, B. Simmons, R. A. Reamer, E. Corley, J. Murry, D. Tschaen, J. Org. Chem., 2008, 73, 312-315.

DOI: 10.1021/jo701877h

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Abstract

A simple, one-pot preparation of cyclic amines via efficient chlorination of amino alcohols with use of SOCl₂ obviates the need for the classical N-protection/O-activation/cyclization/deprotection sequence commonly employed for this type of transformation. The reaction pathways and the general scope of this method have also been investigated.

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Key Words

Pyrrolidines, Piperidines

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ID: J42-Y2008-0170