Synthesis,resolution and absolute configuration of a tolperisone metabolite |
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| Institution: | 1. Department of Organic Chemical Technology, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary;2. Institute of Chemistry, Chemical Research Centre, H.A.S., H-1525 Budapest, PO Box 17, Hungary;1. Institute of Structural Macrokinetics and Materials Science, Russian Academy of Sciences, Chernogolovka, Moscow, 142432 Russia;2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, 119991 Russia;1. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji’nan, Shandong, PR China;2. Department of Pharmacology, School of Medicine, Shandong University, 44 West Culture Road, 250012 Ji’nan, Shandong, PR China;3. Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium;1. Department of Biochemistry, College of Life Science and Biotechnology, Yonsei University, Seoul, Republic of Korea;2. School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea;3. Bioinformatics and Molecular Design Research Center, 120-749 Seoul, Republic of Korea;4. Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, Seoul 120-749, Republic of Korea;1. Department of Organic Chemical Technology, Budapest University of Technology and Economics, Budapest, Hungary;2. MTA-BME Organic Chemical Technology Research Group, Hungarian Academy of Sciences, Department of Organic Chemical Technology, Budapest University of Technology and Economics, Budapest, Hungary |
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| Abstract: | 1-(4′-Hydroxymethyl-phenyl)-2-methyl-3-(piperidine-1-yl)-propane-1-one M2, a metabolite of tolperisone, was synthesised in a solvent-free Mannich reaction. The optical resolution was carried out by diastereoisomeric salt formation and separation, for which three resolving agents ((2R,3R)-O,O′-dibenzoyl tartaric acid, (2R,3R)-O,O′-di-p-toluoyl tartaric acid and (R)-2-hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide (anicyphos)) were found. The absolute configuration of M2 was determined by the single-crystal X-ray diffraction method. |
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