85231-97-6Relevant academic research and scientific papers
New protocol for converting alcohols into amines
Klepacz,Zwierzak
, p. 1683 - 1689 (2007/10/03)
The reactions between diethyl N-(t-butoxycarbonyl)phosphoramidate 1, diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP) and primary or secondary alcohols lead to the corresponding diethyl N-alkyl-N-(t-butoxycarbonyl)phosphoramidates 2a-o. Deprotection of crude 2 by refluxing with p-toluenesulfonic acid monohydrate in ethanol affords ammonium tosylates 3a-o in moderate to good overall yields. The N-alkylation of 1 proceeds stereoselectively with complete inversion of the configuration of the alkyl group.
An optimized version of Gabriel-type nucleophilic amination
Zwierzak, Andrzej
, p. 2287 - 2293 (2007/10/03)
N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t- butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-I. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol-affords ammonium tosylates 3a-I in reasonable yields.
