15430-57-6Relevant academic research and scientific papers
New protocol for converting alcohols into amines
Klepacz,Zwierzak
, p. 1683 - 1689 (2001)
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.
TRIETHYL PHOSPHITE IN ORGANIC SYNTHESIS. A FACILE, ONE-POT CONVERSION OF ALCOHOLS INTO AMINES
Zwierzak, Andrzej
, p. 51 - 54 (2007/10/02)
General protocols for converting primary, secondary, and tertiary alcohols into the corresponding primary amines are presented.
Optimized procedures for one-pot conversion of alkyl bromides into amines via the Staudinger reaction
Koziara,Zwierzak
, p. 1063 - 1065 (2007/10/02)
New optimized procedures for transforming primary and secondary alkyl bromides into the corresponding primary amine salts have been elaborated. Essential modifications of azidation and deprotection of intermediate triethoxyphosphine alkylimides resulted in substantial improvement of the overall yields. Conversion of ammonium tosylates and hydrochlorides into free amines in a nonaqueous medium is described.
