Efficient and single pot process for the preparation of enantiomerically pure solifenacin succinate, an antimuscarinic agent

The development of an efficient and economic one-pot process, in which the configuration of the chiral centers of the starting materials is retained, for the preparation of highly pure solifenacin succinate, an antimuscarinic agent, is presented in this communication. The earlier reported processes...

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Bibliographic Details
Published in:Monatshefte für Chemie 2011-11, Vol.142 (11), p.1181-1186
Main Authors: Niphade, Navnath C., Jagtap, Kunal M., Mali, Anil C., Solanki, Pavankumar V., Jachak, Madhukar N., Mathad, Vijayavitthal T.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Summary:The development of an efficient and economic one-pot process, in which the configuration of the chiral centers of the starting materials is retained, for the preparation of highly pure solifenacin succinate, an antimuscarinic agent, is presented in this communication. The earlier reported processes suffer from the drawbacks of racemization and low yields due to the use of strong base, higher temperatures, and longer reaction times. The present work circumvents these issues by activating (3 R )-quinuclidin-3-ol into a mixed active carbonate derivative by treating it with bis(4-nitrophenyl)carbonate. The subsequent reaction of the active carbonate with an enantiomerically pure amine without using any base at ambient temperature provided enantiomerically pure solifenacin with an overall yield of 90%. Graphical Abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-011-0610-7