An Efficient and Scalable Synthesis of tert-Butyl (3aR,6aS)-5-Oxohexahydrocyclo penta[c]pyrrole-2(1H)-carboxylate: A Pharmacologically Important Intermediate,Organic Process Research & Development

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An Efficient and Scalable Synthesis of tert-Butyl (3aR,6aS)-5-Oxohexahydrocyclo penta[c]pyrrole-2(1H)-carboxylate: A Pharmacologically Important Intermediate
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2017-01-30 00:00:00 , DOI: 10.1021/acs.oprd.6b00399
Rajesh H. Bahekar ₁ , Pradip A. Jadav ₁ , Amitgiri D. Goswami ₁ , Hardik A. Shah ₁ , Bhushan N. Dave ₁ , Darshan A. Joshi ₁ , Jignesh P. Pethani ₁ , Dipam Patel ₁ , Sameer Agarwal ₁ , Ranjit C. Desai ₁

Affiliation

Hexahydrocyclopentapyrrolone derivatives constitute an important class of bicycles, and it represents an essential pharmacophore for diversified pharmacological activities. A highly efficient process for the synthesis of tert-butyl(3aR,6aS)-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 1 has been developed. The improved process involves transformation of isoindole 4 to diacid 5, using an inexpensive KMnO₄ mediated oxidative cleavage as a key step. The developed process was cost-effective, high yielding, kilogram scalable, and commercially viable for synthesis of 1.

中文翻译：

有效和可扩展的叔丁基（3a R，6a S）-5-氧六氢环戊[ c ]吡咯-2（1 H）-羧酸酯的合成：药理学上重要的中间体

六氢环戊吡咯烷酮衍生物构成一类重要的自行车，它代表着多种药理活性的必不可少的药效团。用于合成A高效处理叔丁基（3A - [R，6α小号）-5- oxohexahydrocyclopenta [ C ^ ]吡咯-2（1 ħ） -羧酸叔丁酯1已经研制成功。改进的方法涉及使用廉价的KMnO ₄介导的氧化裂解作为关键步骤，将异吲哚4转化为二酸5。所开发的方法具有成本效益，高收率，千克可分级，并且在商业上可用于合成1。

更新日期：2017-01-30

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