Simple and Efficient Synthesis of (S)-Dapoxetine

Abstract

A refinement in the synthetic strategy for (S)-dapoxetine 1 is described. The key features of synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and regioselective reductive ring opening of a 2,3-epoxy alcohol to elaborate the hydroxy-bearing stereogenic center at benzylic position; (b) regioselective functionalization of 1-naphthol and amine functionality through Mitsunobu procedures; and (c) Eschweiler–Clarke reductive methylation condition to access the target molecule.

GRAPHICAL ABSTRACT

Keywords:

• Intermolecular etherification
• reductive methylation
• Sharpless asymmetric epoxidation

ACKNOWLEDGMENT

The authors are thankful to the Department of Science and Technology for financial support of this research.