Synthesis and Absolute Configuration Assignment of 9-Hydroxyrisperidone Enantiomers

Author(s): Weichu Xu, George E. Wright, Milka Yanachkova, Ivan B. Yanachkov.

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 6 , 2014

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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.

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Article Details

VOLUME: 11
ISSUE: 6
Year: 2014
Page: [470 - 473]
Pages: 4
DOI: 10.2174/1570178611666140219004433
Price: $58

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