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Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures

Ahmed F. Abdel-Magid,* Kenneth G. Carson, Bruce D. Harris, Cynthia A. Maryanoff and Rekha D. Shah

*The R. W. Johnson Pharmaceutical Research Institute, Department of Chemical Development, Spring House, Pennsylvania 19477, Email: amagidprdus.jnj.com

A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem., 1996, 61, 3849-3862.

DOI: 10.1021/jo960057x (free Supporting Information)


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Abstract

Sodium triacetoxyborohydride is a general, mild, and selective reducing agent for the reductive amination of various aldehydes and ketones. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran and occasionally in acetonitrile. Acetic acid may be used as catalyst with ketone reactions. Acid sensitive functional groups such as acetals and ketals, and reducible functional groups such as C-C multiple bonds and cyano and nitro groups are tolerated.

In the reductive amination of some aldehydes with primary amines where dialkylation is a problem, a stepwise procedure involving imine formation in MeOH followed by reduction with NaBH4 was developed.

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Key Words

Reductive Amination, Amines, Aldehydes, Ketones, Sodium triacetoxyborohydride, Sodium borohydride


ID: J42-Y1996-270