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.