A tertiary amine synthesis via a hydroxylamine alkylation/catalytic reduction sequence

Abstract

Overalkylation is a common side reaction that typically prevents the synthesis of tertiary N-methylamines from secondary amines, using alkyl iodides and other reactive electrophiles. Herein, we present an indirect approach featuring hydroxylamines, using a reaction sequence involving alkylation, followed by an optimized, catalytic in situ reduction of the N-oxide intermediate to give the desired N-methyl tertiary amine. An optimized isolation of these products is also reported.