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Molecules 2018, 23(5), 1216; https://doi.org/10.3390/molecules23051216

Improved Synthesis of N-Methylcadaverine

Department of Chemistry and Biochemistry, Texas Tech University, Box 41061, Lubbock, TX 79409-1061, USA
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Academic Editors: Wenxu Zhou and De-an Guo
Received: 25 April 2018 / Revised: 10 May 2018 / Accepted: 15 May 2018 / Published: 19 May 2018
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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. View Full-Text
Keywords: alkaloid; granatane; N-methylcadaverine; N-methylpiperidine. reductive deamination alkaloid; granatane; N-methylcadaverine; N-methylpiperidine. reductive deamination
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Anderson, K.N.; Moaven, S.; Unruh, D.K.; Cozzolino, A.F.; D’Auria, J.C. Improved Synthesis of N-Methylcadaverine. Molecules 2018, 23, 1216.

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