Abstract
The enantiomers of 9-hydroxyrisperidone, the major metabolite of risperidone and the active component of the antipsychotic drug Invega®, were synthesized by efficient methods. Their optical rotation and enantiomeric purity were characterized for the first time. The absolute configurations were assigned by comparing 1H NMR chemical shifts of Mosher esters of a key stereoisomeric intermediate. Thus, the stereoisomeric center of (+)-9-hydroxyrisperidone has been assigned as the S configuration, and its enantiomer has the configuration R.
Keywords: Invega®, 9-hydroxyrisperidone enantiomers, chiral HPLC, absolute configuration, synthesis.
Graphical Abstract
Letters in Organic Chemistry
Title:Synthesis and Absolute Configuration Assignment of 9-Hydroxyrisperidone Enantiomers
Volume: 11 Issue: 6
Author(s): Weichu Xu, George E. Wright, Milka Yanachkova and Ivan B. Yanachkov
Affiliation:
Keywords: Invega®, 9-hydroxyrisperidone enantiomers, chiral HPLC, absolute configuration, synthesis.
Abstract: The enantiomers of 9-hydroxyrisperidone, the major metabolite of risperidone and the active component of the antipsychotic drug Invega®, were synthesized by efficient methods. Their optical rotation and enantiomeric purity were characterized for the first time. The absolute configurations were assigned by comparing 1H NMR chemical shifts of Mosher esters of a key stereoisomeric intermediate. Thus, the stereoisomeric center of (+)-9-hydroxyrisperidone has been assigned as the S configuration, and its enantiomer has the configuration R.
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Cite this article as:
Xu Weichu, E. Wright George, Yanachkova Milka and B. Yanachkov Ivan, Synthesis and Absolute Configuration Assignment of 9-Hydroxyrisperidone Enantiomers, Letters in Organic Chemistry 2014; 11 (6) . https://dx.doi.org/10.2174/1570178611666140219004433
DOI https://dx.doi.org/10.2174/1570178611666140219004433 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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