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KMID : 1059520150590060488
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Journal of the Korean Chemical Society
2015 Volume.59 No. 6 p.488 ~ p.492
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Preparation of (S)-(+)-Pranidipine by Optical Resolution
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Baek Du-Jong
Yoon Ji-Hye
Kim Moon-Sik
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Abstract
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In this study, the effective preparation method of (S)-(+)-pranidipine, the active component of antihypertensive drug as a calcium channel blocker, was developed using optical resolution. The racemic monocarboxylic acid 5 obtained by the hydrolysis of (±)-pranidipine was mixed with optically active quinidine to form salts, and the insoluble diastereomeric salt was collected and successive treatment with base and acid furnished (R)-(-)-carboxylic acid 7. (S)-(+)-Pranidipine was prepared by esterification of this acid with cinnamyl alcohol, and the analysis by chiral HPLC showed 100% enantiomeric excess (ee). This process would be industrially very useful to prepare chiral (S)-(+)-pranidipine, since the use of strong base and anhydrous solvents, and ultra-low temperature condition were excluded in this process.
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KEYWORD
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(S)-(+)-Pranidipine, Calcium channel blocker, Antihypertensive drug, Optical resolution, Enantiomeric excess
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