Improved Synthesis of N-Methylcadaverine

Kayla Anderson; Shiva Moaven; Daniel K. Unruh; Anthony Cozzolino; John D'Auria

Improved Synthesis of N-Methylcadaverine

Kayla Anderson, Shiva Moaven, Daniel K. Unruh, Anthony Cozzolino, John D'Auria

Chemistry and Biochemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1216
Journal	Default journal
State	Published - May 2018

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Anderson, K., Moaven, S., Unruh, D. K., Cozzolino, A., & D'Auria, J. (2018). Improved Synthesis of N-Methylcadaverine. Default journal, 1216.

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AB - 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.

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