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