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Synthesis of 15N-labelled nornicotine and 15N-labelled nicotine

✍ Scribed by Giang Vo-Thanh; François-Xavier Felpin; Gilbert Nourrisson; Michel Trierweiler; Richard J. Robins; Jacques Lebreton

Publisher: John Wiley and Sons
Year: 2001
Tongue: French
Weight: 103 KB
Volume: 44
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.512

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✦ Synopsis

Abstract

The synthesis of ^15^N‐labelled nornicotine 2 and ^15^N‐labelled nicotine 1 is described via the reductive aminocyclization of a 1,4‐ketoaldehyde with a corresponding amine in the presence of sodium cyanoborohydride. Yields of 30% and 26%, respectively, were obtained from 3‐bromopyridine. The ^15^N‐label has been easily introduced from ammonium‐^15^N‐labelled chloride as an inexpensive label source. As far as we are aware, this is the first synthesis of ^15^N‐labelled nicotine. Copyright © 2001 John Wiley & Sons, Ltd.

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