Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1-propanol via resolution with immobilized penicillin G acylase |
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| Institution: | 1. Institut Mines-Télécom (IMT) Lille Douai, Université de Lille, Département Sciences de l’Atmosphère et Génie de l’Environnement (SAGE), F-59500 Lille, France;2. Groupe de Spectrométrie Moléculaire et Atmosphérique (GSMA), UMR CNRS 7331, Université de Reims, F-51687 Reims, France;3. Université Lille, CNRS, UMR 8522, Physicochimie des Processus de Combustion et de l’Atmosphère (PC2A), F-59000 Lille, France;1. School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China;2. Department of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China;1. Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, China;2. Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637009, China;3. Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China;4. Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai 200433, China;5. Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr 45470, Germany |
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| Abstract: | Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker’s yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee >99%) and >45% yields for each enantiomer. |
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