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

  title={An improved synthesis of (+/-)-N'-nitrosonornicotine 5'-acetate.},
  author={Gwendolyn A Marriner and Sean M. Kerwin},
  journal={The Journal of organic chemistry},
  volume={74 7},
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.