Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis of N-Substituted Cyclic Amines

Michael C. Venuti; Oswald Ort

doi:10.1055/s-1988-27777

Synthesis 1988; 1988(12): 985-988
DOI: 10.1055/s-1988-27777

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Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis of N-Substituted Cyclic Amines

Michael C. Venuti^* , Oswald Ort

^*Institute of Bio-Organic Chemistry, Syntex Research, 3401 Hillview Avenue, Palo Alto, CA 94 304, USA

Abstract

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Borane-methyl sulfide (BMS) reduction of variously N-substituted succinamic and glutaramic esters affords the corresponding N-substituted pyrrolidines and piperidines in high yields. The limitations, mainly caused by steric hinderance around the amine nitrogen, and putative intermediates involved in this conversion, as detected by incomplete reaction and/or synthesis followed by BMS reduction, indicate that cyclization and amide reduction successfully compete with ester reduction to afford the N-substituted cyclized amines.

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