A one-pot selective synthesis of N-Boc protected secondary amines: tandem direct reductive amination/N-Boc protection

R Neelarapu, PA Petukhov

Index: Neelarapu, Raghupathi; Petukhov, Pavel A. Tetrahedron, 2012 , vol. 68, # 35 p. 7056 - 7062

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Citation Number: 2

Abstract

A one-pot tandem direct reductive amination of aldehydes with primary amines resulting in N- Boc secondary amines using a (Boc) 2O/sodium triacetoxyborohydride (STAB) system is reported. The tandem procedure is efficient, selective, and versatile, giving excellent yields of N-Boc protected secondary amines even in those cases where the products are prone to intramolecular lactamization.