An optimized protocol for the multigram synthesis of 3-(trifluoromethyl)bicyclo[1.1.1]pent-1-ylglycine (CF3-Bpg) |
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Authors: | Pavel K. Mykhailiuk Nataliia M. Voievoda Sergii Afonin Igor V. Komarov |
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Affiliation: | a Department of Chemistry, Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, 01033 Kyiv, Ukraine b Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine c Karlsruhe Institute of Technology (KIT), Forschungszentrum Karlsruhe, Institut für Biologische Grenzflächen, POB 3640, 76021 Karlsruhe, Germany d KIT, Universität Karlsruhe, Institut für Organische Chemie, Fritz-Haber-Weg 6, 76133 Karlsruhe, Germany |
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Abstract: | An optimized procedure for the multigram synthesis of 3-(trifluoromethyl)bicyclo[1.1.1]pent-1-ylglycine (CF3-Bpg) has been developed. The overall yield of the synthesis for the optimized up-scaling was increased from 35% to 53%. Moreover, conditions for separating the key isomeric aminonitriles 7 and 8 by crystallization were found, which greatly facilitated the isolation of 8 on a multigram scale. Following this optimized protocol, 100 g of optically pure CF3-Bpg have been synthesized. |
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Keywords: | Fluorine Amino acids Conformational rigidity Large-scale synthesis |
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