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

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

The Journal of organic chemistry (2009-03-11)

Gwendolyn A Marriner, Sean M Kerwin

PMID19271724

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.

MATERIALS

Product Number

Brand

Product Description

75285

Supelco

N′-Nitrosonornicotine, analytical standard

N-075

Supelco

(±)-N′-Nitrosonornicotine (NNN) solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant^®