Optical Resolution and Optimization of (R,S)‐Propranolol Using Dehydroabietic Acid Via Diastereomeric Crystallization |
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Authors: | Li Ge Qiongqiong Zhao Kedi Yang Shishi Liu Fan Xia |
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Affiliation: | School of Chemistry & Chemical Engineering, Guangxi University, Nanning, China |
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Abstract: | The optical resolution of (R,S)‐propranolol by the diastereomeric crystallization method was successfully performed using dehydroabietic acid (DHAA) as the resolving agent in methanol. The three important parameters: DHAA amount, solvent (methanol) amount, and crystallization temperature of diastereomeric salts were optimized employing the response surface methodology (RSM). When maintaining a lower limit of 95% for the purity of (S)‐propranolol, the optimal resolution conditions were a DHAA/(R,S)‐propranolol molar ratio of 1.1, solvent/(R,S)‐propranolol ratio of 16.2 mL.g‐1, and crystallization temperature of –5 °C. The desired (S)‐propranolol was prepared with 94.8% optical purity and 72.2% yield under the optimal conditions. Chirality 27:131–136, 2015. © 2014 Wiley Periodicals, Inc. |
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Keywords: | propranolol dehydroabietic acid resolution optimization response surface methodology |
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