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A New Route to Bicyclo[1.1.1]pentan-1-amine from 1-Azido-3-iodobicyclo[1.1.1]pentane
Organic Letters ( IF 4.9 ) Pub Date : 2014-03-14 00:00:00 , DOI: 10.1021/ol500635p
Yi Ling Goh 1 , Eric K.W. Tam 1 , Paul H. Bernardo 1 , Choon Boon Cheong 1 , Charles W. Johannes 1 , Anthony D. William 1 , Vikrant A. Adsool 1
Affiliation  

From a medicinal chemistry perspective, bicyclo[1.1.1]pentan-1-amine (1) has served as a unique and important moiety. Synthetically, however, this compound has received little attention, and only one scalable route to this amine has been demonstrated. Reduction of an easily available and potentially versatile intermediate, 1-azido-3-iodobicyclo[1.1.1]pentane (2), can offer both a flexible and scalable alternative to this target. Herein, we describe our scrutiny of this reportedly elusive transformation and report our ensuing success with this endeavor.

中文翻译:

从1-叠氮基-3-碘代双环[1.1.1]戊烷合成双环[1.1.1]戊丹-1-胺的新途径

从药物化学的观点来看,双环[1.1.1]戊丹-1-胺(1)已经用作独特且重要的部分。但是,从合成上讲,该化合物几乎没有受到关注,并且仅证明了一种可扩展的途径来制备该胺。减少易获得且可能通用的中间体1-azido-3-iodobicyclo [1.1.1]戊烷(2),可以为该目标提供灵活且可扩展的替代方案。在这里,我们描述了我们对这种难以捉摸的转变的审查,并报告了我们在这项努力中取得的成功。
更新日期:2014-03-14
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