Selective N-dealkylation of tertiary amines derived from phenylglycinol orephedrine family

Authors
Agami, C Couty, F Evano, G
Citation
C. Agami et al., Selective N-dealkylation of tertiary amines derived from phenylglycinol orephedrine family, TETRAHEDR L, 40(19), 1999, pp. 3709-3712
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
19
Year of publication
1999
Pages
3709 - 3712
Database
ISI
SICI code
0040-4039(19990507)40:19<3709:SNOTAD>2.0.ZU;2-E
Abstract
Tertiary amines bearing an hydroxyethyl group derived from phenylglycinol, norephedrine or norpseudoephedrine can be selectively dealkylated using a t wo-step sequence involving treatment with thionyl chloride in THF, followed by reaction with an excess of potassium cyanide in THF:DMSO. These conditi ons are compatible with the presence of an insaturation or a benzyl ether i n the substrate. (C) 1999 Published by Elsevier Science Ltd. All rights res erved.