Synthesis 2014; 46(20): 2794-2798
DOI: 10.1055/s-0034-1378515
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Total Syntheses of Solifenacin and N-Acetyl-1-(4-chloro­phenyl)-6,7-dimethoxytetrahydroisoquinoline

R. Anji Babu
a   Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
b   Department of Organic Chemistry, Adikavi Nannaya University, Rajahmundry 533105, India   Email: basireddy@iict.res.in
,
N. Siva Senkar Reddy
a   Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
b   Department of Organic Chemistry, Adikavi Nannaya University, Rajahmundry 533105, India   Email: basireddy@iict.res.in
,
B. Jagan Mohan Reddy
b   Department of Organic Chemistry, Adikavi Nannaya University, Rajahmundry 533105, India   Email: basireddy@iict.res.in
,
B. V. Subba Reddy*
a   Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
› Author Affiliations
Further Information

Publication History

Received: 19 May 2014

Accepted after revision: 24 June 2014

Publication Date:
16 July 2014 (online)


Abstract

A highly stereoselective synthesis of 1-aryl-1,2,3,4-tetrahydroisoquinoline drugs such as solefinacin (muscarinic acetylcholine receptor antagonist) and N-acetyl-1-(4-chlorophenyl)-6,7-dimethoxytetrahydroisoquinoline (AMPA receptor antagonist) has been accomplished using (R)-tert-butanesulfinamide as a chiral source. Chiral tetrahydroisoquinolines have been prepared through the aryl Grignard addition to chiral N-sulfinylimines followed by haloamide cyclization.

Supporting Information

 
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