Improved synthesis of n-methylcadaverine

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

Research output: Contribution to journalArticle

Abstract

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
JournalMolecules
Volume23
Issue number5
DOIs
StatePublished - 2018

Keywords

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

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    Anderson, K. N., Moaven, S., Unruh, D. K., Cozzolino, A. F., & D’Auria, J. C. (2018). Improved synthesis of n-methylcadaverine. Molecules, 23(5), [1216]. https://doi.org/10.3390/molecules23051216