Journal
ORGANIC LETTERS
Volume 13, Issue 17, Pages 4746-4748Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201883z
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The reaction of [1.1.1]propellane with di-tert-butyl azodicarboxylate and phenylsliane 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.
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