Convenient procedure for one-pot conversion of azides to N-monomethylamines

Citation
H. Kato et al., Convenient procedure for one-pot conversion of azides to N-monomethylamines, SYNLETT, 2001, pp. 1003-1005
Citations number
13
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
0936-5214 → ACNP
Year of publication
2001
Pages
1003 - 1005
Database
ISI
SICI code
0936-5214(2001):<1003:CPFOCO>2.0.ZU;2-I
Abstract
One-pot conversion of azides to N-monomethylamines is described. Two option al protocols have been developed, which share the first stage, the reaction of an azide with (CH3)(3)P to generate the corresponding iminophosphorane. This Staudinger intermediate, thus generated, is either methylated with CH 3I and hydrolyzed (method A), or treated with (HCHO)(n) and reduced with Na BH4 (method B), thereby giving the corresponding N-monomethylamine in high yield.