title: An improved synthesis of (+/-)-N'-nitrosonornicotine 5'-acetate.
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.
authors.affiliation: College of Pharmacy and Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Gwendolyn A
authors.initials: GA
authors.lastname: Marriner
authors.forename: Sean M
authors.initials: SM
authors.lastname: Kerwin
mesh_terms: D015394:Molecular Structure; D009602:Nitrosamines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C540297:N'-nitrosonornicotine 5'-acetate; D009602:Nitrosamines; C008655:N'-nitrosonornicotine