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Scalable Synthesis of 1-Bicyclo[1.1.1]pentylamine via a Hydrohydrazination Reaction
Organic Letters ( IF 4.9 ) Pub Date : 2011-08-11 00:00:00 , DOI: 10.1021/ol201883z Kevin D. Bunker 1 , Neal W. Sach 1 , Qinhua Huang 1 , Paul F. Richardson 1
Organic Letters ( IF 4.9 ) Pub Date : 2011-08-11 00:00:00 , DOI: 10.1021/ol201883z Kevin D. Bunker 1 , Neal W. Sach 1 , Qinhua Huang 1 , Paul F. Richardson 1
Affiliation
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.
中文翻译:
通过氢酰肼化反应可扩展合成1-双环[1.1.1]戊胺
[1.1.1]螺桨烷与二的反应叔丁基偶氮二羧酸酯和苯基硅烷中的Mn(DPM)的存在3,得到二-叔丁基1-(二环[1.1.1]戊-1-基)肼描述了-1,2-二羧酸酯。随后的脱保护得到1-双环[1.1.1]戊基肼,然后还原得到1-双环[1.1.1]戊基胺。在可扩展性,产率,安全性和成本方面,所报道的路线标志着对先前的1-双环[1.1.1]戊胺合成的显着改进。
更新日期:2011-08-11
中文翻译:
通过氢酰肼化反应可扩展合成1-双环[1.1.1]戊胺
[1.1.1]螺桨烷与二的反应叔丁基偶氮二羧酸酯和苯基硅烷中的Mn(DPM)的存在3,得到二-叔丁基1-(二环[1.1.1]戊-1-基)肼描述了-1,2-二羧酸酯。随后的脱保护得到1-双环[1.1.1]戊基肼,然后还原得到1-双环[1.1.1]戊基胺。在可扩展性,产率,安全性和成本方面,所报道的路线标志着对先前的1-双环[1.1.1]戊胺合成的显着改进。