A scalable and expedient method of preparing diastereomerically and enantiomerically enriched pseudonorephedrine from norephedrine |
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| Affiliation: | 1. Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain;2. Department of Pharmacology, Medical School, University of Patras, 26500 Rio-Patras, Greece;1. Department of Chemistry, R. K. Mission Vivekananda Centenary College, Rahara, Kolkata 700 118, West Bengal, India;2. Chemistry Division, CSIR-Indian Institute of Chemical Biology, Jadavpur 700 032, West Bengal, India;3. Department of Chemistry, The University of Reading, PO Box 224, Whiteknights, Reading RG6 6AD, UK;1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation;2. Bashkir State University, Zaki Validi Street 32, 450076 Ufa, Russian Federation |
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| Abstract: | Norephedrine has been efficiently converted into the corresponding diastereomer pseudonorephedrine using a three step, one-pot reaction. The three step process involves treatment of norephedrine with di-tert-butyl dicarbonate (Boc2O); cyclization by way of mesylate formation at the alcohol; and lithium hydroxide mediated hydrolysis of the oxazolidinone. The diastereomeric purity was determined by HPLC and the enantiomeric purity was determined by optical activity measurements and chiral stationary phase HPLC analysis of the pseudonorephedrine oxazolidinone derivatives. |
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