First preparation of enantiomerically pure sibutramine and its major metabolite, and determination of their absolute configuration by single crystal X-ray analysis

Authors
Fang, QK Senanayake, CH Han, ZX Morency, C Grover, P Malone, RE Bulter, H Wald, SA Cameron, TS
Citation
Qk. Fang et al., First preparation of enantiomerically pure sibutramine and its major metabolite, and determination of their absolute configuration by single crystal X-ray analysis, TETRAHEDR-A, 10(23), 1999, pp. 4477-4480
Citations number
6
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
23
Year of publication
1999
Pages
4477 - 4480
Database
ISI
SICI code
0957-4166(199912)10:23<4477:FPOEPS>2.0.ZU;2-N
Abstract
Racemic sibutramine was resolved with dibenzoyl-D-tartaric acid, and the ab solute stereochemistry of sibutramine was determined by single crystal X-ra y crystallography of its dibenzoyl D-tartrate. The major active metabolite (desmethylsibutramine) was obtained by demethylation of sibutramine with DE AD. Enantiomeric purity of sibutramine was determined by HPLC on an Ultron ES-OVM column. (C) 1999 Elsevier Science Ltd. All rights reserved.