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Synthesis 2009(23): 4032-4036  
DOI: 10.1055/s-0029-1217050
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Expedient Reductive Amination of Aldehyde Bisulfite Adducts

Chennagiri R. Pandit, Neelakandha S. Mani*
Department of Drug Discovery, Johnson & Johnson Pharmaceuticals Research and Development, L.L.C., 3210 Merryfield Row, San Diego, CA 92121, USA
Fax: +1(858)3203354; e-Mail: nmani@its.jnj.com;
Further Information

Publication History

Received 29 May 2009
Publication Date:
03 November 2009 (online)

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Abstract

A novel, one-pot protocol for the direct reductive amination of aldehyde bisulfite adducts is reported. Bisulfite adducts of aliphatic and aromatic aldehydes, on treatment with an organic base under non-aqueous conditions liberate the aldehyde in situ, which then undergoes efficient reductive amination with amines in the presence of sodium triacetoxyborohydride.

Key words

Bisulfite adducts - reductive amination - sodium triacetoxyborohydride

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