An improved synthesis of (+/-)-N'-nitrosonornicotine 5'-acetate

Gwendolyn A Marriner; Sean M Kerwin

doi:10.1021/jo9000417

An improved synthesis of (+/-)-N'-nitrosonornicotine 5'-acetate

J Org Chem. 2009 Apr 3;74(7):2891-2. doi: 10.1021/jo9000417.

Authors

Gwendolyn A Marriner¹, Sean M Kerwin

Affiliation

¹ College of Pharmacy and Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.

PMID: 19271724
DOI: 10.1021/jo9000417

Abstract

A concise and efficient route to (+/-)-N'-nitrosonornicotine 5'-acetate (NNN-5'-OAc), a stable precursor of the active metabolite 5'-hydroxy(+/-)-N'-nitrosonornicotine NNN-5'-OH is reported. The synthesis utilizes sulfinimine chemistry to give (+/-)-NNN-5'-OAc in 26% yield over 4 steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Structure
Nitrosamines / chemical synthesis*
Nitrosamines / chemistry

Substances

N'-nitrosonornicotine 5'-acetate
Nitrosamines
N'-nitrosonornicotine