An optimized protocol for the multigram synthesis of 3-(trifluoromethyl)bicyclo[1.1.1]pent-1-ylglycine (CF3-Bpg)

作者：Mykhailiuk Pavel K^*; Voievoda Nataliia M; Afonin Sergii; Ulrich Anne S; Komarov Igor V

来源：Journal of Fluorine Chemistry, 2010, 131(2): 217-220.

DOI：10.1016/j.jfluchem.2009.10.004

• Fluorine
• Amino acids
• Conformational rigidity
• Large-scale synthesis

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.

• 出版日期2010-2