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Reductive Alkylation of Hydrazine Derivatives with α-Picoline-Borane and Its Applications to the Syntheses of Useful Compounds Related to Active Pharmaceutical­ Ingredients

Yasushi Kawase, Takehiro Yamagishi, Jun-ya Kato, Teruo Kutsuma, Tadashi Kataoka, Takeo Iwakuma, Tsutomu Yokomatsu*

*School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan, Email:

Y. Kawase, T. Yamagishi, J.-y. Kato, T. Kutsuma, T. Kataoka, T. Iwakuma, T. Yokomatsu, Synthesis, 2014, 46, 455-464.

DOI: 10.1055/s-0033-1340484

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An efficient method for the direct reductive alkylation of hydrazine derivatives with α-picoline-borane provided various N-alkylhydrazine derivatives upon fine-tuning of the substrates and the reagent equivalency in a one-pot manner. The method was applied to the synthesis of active pharmaceutical ingredients of therapeutic drugs such as isocarboxazid.

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Key Words

hydrazine derivatives, α-picoline-borane, reductive amination

ID: J66-Y2014