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Synthesis 2010(1): 36-42  
DOI: 10.1055/s-0029-1217076
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Reductive N-Alkylation with Carbonyl Compounds To Give Tertiary Amines via Borane Reduction of Imines

Masashi Tokizanea, Kaori Satoa, Yuki Sakamia, Yoichiro Imoria, Chika Matsuoa, Tetsuo Ohta*b, Yoshihiko Itoa
a Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan
b Department of Biomedical Information, Faculty of Life and Medical Sciences, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan
Fax: +81(774)656789; e-Mail: tota@mail.doshisha.ac.jp;
Further Information

Publication History

Received 5 August 2009
Publication Date:
22 October 2009 (online)

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Abstract

One-pot synthesis of tertiary amines via borane-mediated reduction of imines and reductive N-alkylation with carbonyl compounds is described. This protocol’s reducing agent is only borane in the reduction of imines, and additional reductant is not necessary in reductive N-alkylation step. When using more than two equivalents of aldehydes, reductive N-alkylation proceeded in good yield.

Key words

reductive N-alkylation - borane reduction - imines - tertiary amines - one-pot reaction

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