Enantioselective synthesis of (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B

An efficient biocatalytic process has been developed to obtain optically pure (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol which can be used as the key intermediate of ticagrelor. In this research, several N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol derivatives have been investigated in which Candida antarctica lipase B (CALB) was used to catalyze the asymmetric hydrolysis reaction. As expected, some of these substrates successfully gave (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol in >98% enantiomeric excess (ee) with conversion yields up to 45%.

Graphical abstractAn efficient biocatalytic process to obtain optically active (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol was developed by employing CALB as the catalyst and using several N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol derivatives as substrates.Figure optionsDownload full-size imageDownload as PowerPoint slide