Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


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.

see article for more examples



Key Words

Pyrrolidines, Piperidines


ID: J42-Y2008-0170