A General One-Pot, Three-Component Mono N-Alkylation of Amines and Amine Derivatives in Lithium Perchlorate/Diethyl Ether Solution

Abstract An efficient, general procedure for reductive monoalkyl­ation of amines and amine derivatives with aldehydes is reported. Treatment of aldehydes with primary amines, secondary amines, O-trimethylsilylhydroxylamine, and N,N-dimethylhydrazine in lithium perchlorate/diethyl ether and trimethylsilyl chloride, followed by BH 3 ·NEt 3 reduction, and straightforward workup afforded secondary amines, tertiary amines, N-substituted hydroxylamines, and hydrazines, respectively. Reductive alkylation of α-amino esters with aldehydes afforded the corresponding N-monoalkylated α-amino esters selectively.