Selective Access to Secondary Amines by a Highly Controlled Reductive Mono-N-Alkylation of Primary Amines

Hephzibah J. Kumpaty; Sukanta Bhattacharyya; Erik W. Rehr; Amelia M. Gonzalez

doi:10.1055/s-2003-41066

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Synthesis 2003(14): 2206-2210
DOI: 10.1055/s-2003-41066

PAPER

Selective Access to Secondary Amines by a Highly Controlled Reductive Mono-N-Alkylation of Primary Amines

Hephzibah J. Kumpaty^a, Sukanta Bhattacharyya*^b, Erik W. Rehr^a, Amelia M. Gonzalez^a
^a Department of Chemistry, University of Wisconsin-Whitewater, WI-53190, USA
^b Argonaut Technologies, 1101 Chess Drive, Foster City, CA 94404, USA
e-Mail: sbhattacharyya@argotech.com;

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Publication History

Received 20 May 2003
Publication Date:
24 September 2003 (online)

Abstract
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Abstract

A selective and direct access to secondary amines is reported by reductive mono-N-alkylation of primary amines in the presence of Ti(i-PrO)₄ and NaBH₄. Secondary amines are obtained exclusively from a set of carbonyl compounds and primary amines, demonstrating high chemoselectivity toward reductive mono-N-alkylation.

Key Words

mono-N-alkylation - secondary amines - titanium(IV) isopropoxide - sodium borohydride

References

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15

The work was presented in part, by Kumpaty, H.; Rehr, E. W.; Bhattacharyya, S.; Gonzalez, A. Riege, J. A.; 219th ACS National Meeting; ACS: San Francisco, CA, March 2000; paper CHED-295.