Stereocontrolled synthesis of the enantiomers of 1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)-propyl]-pyrrolidin-2-one |
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| Institution: | 1. Department of Pharmaceutical Chemistry, Collegium Medicum Jagiellonian University, ul. Medyczna 9, 30-688 Kraków, Poland;2. Institut für Pharmazie und Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany;1. Y.B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Aurangabad 431001, M.S., India;2. Department of Biotechnology, Savitribai Phule Pune University, Pune 411007, M.S., India;3. Shivaji University, Vidyanagar, Kolhapur 416 004, M.S., India;1. Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil;2. USDA, ARS, Poisonous Plant Research Laboratory, 1150 East 1400 North, Logan, UT 84341, USA;3. Departamento de Química Fundamental, Universidade Federal de Pernambuco, Avenida Professor Moraes Rego, 1235, CEP 50670-901, Recife, PE, Brazil;4. Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Juiz de Fora, Campus Martelos, CEP 36036-330, Juiz de Fora, MG, Brazil;5. Centro de Biotecnologia and Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil;6. Herbário da UFRN, Universidade Federal do Rio Grande do Norte, Campus Universitário Lagoa Nova, CEP 59078-970, Natal, RN, Brazil;7. Laboratório de Pesquisa em Parasitologia, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil;1. Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine;2. Taras Shevchenko National University of Kyiv, Volodymyrska Street, 60, Kyiv 01601, Ukraine;1. Beijing Key Laboratory of Antimicrobial Agents, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China;2. Qingdao Municipal Hospital, Qingdao 266011, China;1. Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/CHPNR, Department of Chemistry, Faculty of Science of Monastir, 5000 Monastir, Tunisia;2. Laboratoire des maladies transmissibles et des substances biologiquement actives, Faculté de pharmacie, 5000 Monastir, Tunisia;3. Institut UTINAM ‒ UMR CNRS 6213, Université Bourgogne Franche-Comté, 16, route de Gray, 25030 Besançon, France;4. Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany |
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| Abstract: | The asymmetric synthesis of 1-2-hydroxy-3-(4-phenyl-1-piperazinyl)-propyl]-pyrrolidin-2-one 1 is described. Enantiomers of compound 1 were obtained using the Sharpless asymmetric dihydroxylation (AD) or hydrolytic kinetic resolution (HKR) methods. The enantiomers of compound 1, which were obtained by HKR had higher enantiomeric excesses than those which were synthesized by AD and epoxidation. The enantiomeric purity of the synthesized compounds was determinated by capillary electrophoresis. |
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