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

*Argonaut Technologies, 1101 Chess Drive, Foster City, CA 94404, USA, Email: sbhattacharyyaargotech.com

H. J. Kumpaty, S. Bhattacharyya, E. W. Rehr, A. M. Gonzalez, Synthesis, 2003, 2206-2210.

DOI: 10.1055/s-2003-41066

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Abstract

A selective and direct access to secondary amines by reductive mono-N-alkylation of primary amines with carbonyl compounds in the presence of Ti(i-PrO)₄ and NaBH₄ gave exclusively secondary amines.

see article for more examples

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Chemoselective reductive alkylation of ammonia with carbonyl compounds: synthesis of primary and symmetrical secondary amines

B. Miriyala, S. Bhattacharyya, J. S. Williamson, Tetrahedron, 2004, 60, 1463-1471.

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Key Words

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

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ID: J66-Y2003-2010