t-Butyl methyl iminodicarboxylate potassium salt: a modified Gabriel reagent for the introduction of t-butoxycarbonylamino groups

Abstract

t-Butyl methyl iminodicarboxylate potassium salt is a stable, easily prepared, non hygroscopic compound; it undergoes smooth N-alkylation in dipolar aprotic solvents to give derivatives which suffer loss of the methoxycarbonyl group on mild treatment with alkali, enabling the direct conversion R–X → R–NHBoc (Boc = t-butoxycarbonyl) to be achieved.