Organic Process Research and Development p. 266 - 272 (2017)
Update date:2022-08-16
Topics:
Bahekar, Rajesh H.
Jadav, Pradip A.
Goswami, Amitgiri D.
Shah, Hardik A.
Dave, Bhushan N.
Joshi, Darshan A.
Pethani, Jignesh P.
Patel, Dipam
Agarwal, Sameer
Desai, Ranjit C.
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.
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