Preparation of highly enantiopure stereoisomers of 1-(2,6-dimethylphenoxy)-2-aminopropane (mexiletine)

Citation
R. Aav et al., Preparation of highly enantiopure stereoisomers of 1-(2,6-dimethylphenoxy)-2-aminopropane (mexiletine), TETRAHEDR-A, 10(15), 1999, pp. 3033-3038
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
15
Year of publication
1999
Pages
3033 - 3038
Database
ISI
SICI code
0957-4166(19990730)10:15<3033:POHESO>2.0.ZU;2-X
Abstract
Mexiletine [1-(2,6-dimethylphenoxy)-2-aminopropane], an orally effective an tiarrhythmic agent, exhibits enantioselective pharmacokinetics and pharmaco dynamics during mexiletine therapy. The purpose of this paper is to emphasi ze the advantage of tetrahydropyranyl-protected mandelic acid (THPMA) in th e resolution of mexiletine enantiomers. Both enantiomers of mexiletine were obtained in 99% enantiomeric excess. Judging by the differential shielding effects in the H-1 and C-13 NMR analyses, we have observed the opposite pr edominant conformation for the mexiletine mandelates in comparison with the O-methylmandelates. (C) 1999 Elsevier Science Ltd. All rights reserved.