Scalable Synthesis of 1-Bicyclo[1.1.1]pentylamine via a Hydrohydrazination Reaction

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• 作者：Kevin D. Bunker ; Neal W. Sach ; Qinhua Huang ; Paul F. Richardson
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：September 2, 2011
• 年：2011
• 卷：13
• 期：17
• 页码：4746-4748
• 全文大小：694K
• 年卷期：v.13,no.17(September 2, 2011)
• ISSN：1523-7052

文摘

The reaction of [1.1.1]propellane with di-tert-butyl azodicarboxylate and phenylsilane in the presence of Mn(dpm)₃ to give di-tert-butyl 1-(bicyclo[1.1.1]pentan-1-yl)hydrazine-1,2-dicarboxylate is described. Subsequent deprotection gives 1-bicyclo[1.1.1]pentylhydrazine followed by reduction to give 1-bicyclo[1.1.1]pentylamine. The reported route marks a significant improvement over the previous syntheses of 1-bicyclo[1.1.1]pentylamine in terms of scalability, yield, safety, and cost.