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Synthesis 2007(10): 1481-1484  
DOI: 10.1055/s-2007-966026
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Resolution of the Benzomorphan-Based Kappa Opioid Agonist Bremazocine

James B. Thomas, Lawrence E. Brieaddy, Karl G. Boldt, Carin Perretta, F. Ivy Carroll*
Center for Organic and Medicinal Chemistry, Research Triangle Institute, P. O. Box 12194, Research Triangle Park, NC 27709, USA
Fax: +1(919)5418868; e-Mail: fic@rti.org;
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Publication History

Received 21 December 2006
Publication Date:
02 May 2007 (online)

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Abstract

An efficient synthesis of racemic bremazocine hydrochloride salt was developed. The racemic material was resolved using (+)- and (-)-3-bromocamphorsulfonic acid ammonium salt to give optically pure samples of (-)- and (+)-bremazocine.

Key words

bremazocine - kappa opioid agonist - synthesis - medicinal chemistry - receptors