Improved synthesis of n-methylcadaverine

Kayla N. Anderson, Shiva Moaven, Daniel K. Unruh, Anthony F. Cozzolino, John C. D’Auria

Research output: Contribution to journalArticlepeer-review


Alkaloids compose a large class of natural products, and mono-methylated polyamines are a common intermediate in their biosynthesis. In order to evaluate the role of selectively methylated natural products, synthetic strategies are needed to prepare them. Here, N-methylcadaverine is prepared in 37.3% yield in three steps. The alternative literature two-step strategy resulted in reductive deamination to give N-methylpiperidine as determined by the single crystal structure. A straightforward strategy to obtain the mono-alkylated aliphatic diamine, cadaverine, which avoids potential side-reactions, is demonstrated.

Original languageEnglish
Article number1216
Issue number5
StatePublished - 2018


  • Alkaloid
  • Granatane
  • N-methylcadaverine
  • N-methylpiperidine. reductive deamination


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