Title:A Linear and Stereoselective Approach for the Synthesis of Dapoxetine
from Benzaldehyde
Volume: 21
Issue: 11
Author(s): Ramakoteswara Rao Chinta, Kumaraswamy Paridala*Vijay Kumar Tulam
Affiliation:
- UQUIFA India Pvt. Ltd., Discovery
building, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, India
Keywords:
SSRI, dapoxetine, Ellman's sulfinamide, (S, E)-N-Benzylidenesulfinamide, linear synthesis, diastereoselective allylation, asymmetric synthesis.
Abstract: In addition to providing a succinct pathway for the stereoselective synthesis of dapoxetine,
a potent SSRI employed in the treatment of premature ejaculation, this study highlights the strategic
use of Ellman's sulfinamide as a chiral auxiliary. The key method involves the diastereoselective
allylation of (S,E)-N-Benzylidenesulfinamide, resulting in the desired S-configuration critical for the
pharmacological activity of dapoxetine. The utilization of readily available benzaldehyde as the starting
material and 1-naphthol as a late-stage coupling partner contributes to the economic feasibility of
the synthesis. Especially, the linear synthetic approach adopted in this study employs simplified and
more efficient protocols for various transformations, culminating in an overall yield of 26%. This
research not only presents a practical synthetic route for dapoxetine, but also underscores the importance
of cost-effective and streamlined methodologies in drug development processes.
