Lipase-catalyzed kinetic and dynamic kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid |
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| Affiliation: | 1. Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös 6, H-6720 Szeged, PO Box 427, Hungary;2. Department of Pharmacology, Drug Development and Therapeutics/Laboratory of Synthetic Drug Chemistry, University of Turku, Lemminkäisenkatu 5C, FIN-20250, Turku, Finland |
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| Abstract: | A dynamic kinetic resolution method for the preparation of enantiopure 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (R)-2 was developed involving the CAL-B-catalyzed enantioselective hydrolysis of the corresponding ethyl ester (±)-1 in toluene/acetonitrile (4:1) containing 1 equiv of added water and 0.25 equiv of dipropylamine. This method allowed the preparation of (R)-2 (ee = 96%) with 80% isolated yield. The kinetic resolution of (±)-1 in diisopropyl ether at 3 °C afforded both enantiomers with ee ⩾92%. |
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