- Improved Synthesis of N-Methylcadaverine.
Improved Synthesis of N-Methylcadaverine.
Molecules (Basel, Switzerland) (2018-05-23)
Kayla N Anderson, Shiva Moaven, Daniel K Unruh, Anthony F Cozzolino, John C D'Auria
PMID29783733
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.
MATERIALI