Racemization of (S)-(+)-10,11-dimethoxyaporphine and (S)-(+)-aporphine: efficient preparations of (R)-(?)-apomorphine and (R)-(?)-aporphine via a recycle process of resolution |
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| Institution: | 1. Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand;2. Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand;3. Department of Physiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand;4. Mahidol University, Kanchanaburi Campus, Saiyok, Kanchanaburi 71150, Thailand;5. The Forest Herbarium National Park, Wildlife and Plant Conservation Department, Ministry of Natural Resources and Environment, Bangkok, Thailand;1. Department of Chemistry, Fudan University, Shanghai 200433, People’s Republic of China;2. College of Pharmacy, Yanbian University, Yanji 133000, People’s Republic of China;3. Institute of Biomedical Science, Fudan University, Shanghai 200433, People’s Republic of China;4. Rega Institute for Medical Research, Katholieke Universiteit Leuven, 10 Minderbroedersstraat, B-3000 Leuven, Belgium;1. Center for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong 793 022, India;2. Department of Chemistry, University of Washington, Seattle, WA 98195, USA |
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| Abstract: | Efficient preparations of (R)-(?)-apomorphine (R)-1 and (R)-(?)-aporphine (R)-2 based on a recycle process of resolution are described. In this recycle process of resolution, (RS)-(±)-10,11-dimethoxyaporphine 3 as the precursor of 1, and (RS)-(±)-aporphine 2 were successfully resolved into both enantiomers with (+)-dibenzoyltartaric acid (DBTA). The desired (R)-3 and (R)-2 were obtained and then, respectively, transformed to compound (R)-1, the hydrochloride salt of (R)-1, diacetate compound 4 and the hydrochloride salt of (R)-2; while the undesired (S)-3 and (S)-2 were racemized to obtain a racemate, which was suitable for further resolution. A method for the racemization of the undesired (S)-3 and (S)-2 was extensively studied, in order to obtain high-yielding racemization conditions. A plausible mechanism for the racemization of (S)-3 and (S)-2 was also proposed. |
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