An Approach to the Synthesis of a Hepatitis C Virus Inhibitor through a Proline-Catalyzed 1,3-Dipolar Cycloaddition Using Acrolein

Abstract

An efficient and easy protocol for performing 1,3-dipolar cycloaddition using azomethine ylides and acrolein is presented. The reaction catalyzed by d-proline allows the synthesis of C-3 unsubstituted pyrrolidines. The application of this methodology to the synthesis of an advanced intermediate in the preparation of a Hepatitis C virus inhibitor is presented. Final attempts to complete the synthesis of the target inhibitor results in the preparation of its C-4 epimer in good overall yield.

Key words

prolinol - cycloaddition - dipole - pyrrolidine - aminomalonate - acrolein - ylides

Publication History

Received: 15 October 2021

Accepted after revision: 15 November 2021

Article published online:
06 December 2021

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