Recombinant Pig Liver Esterase-Catalyzed Synthesis of (1S,4R)-4-Hydroxy-2-cyclopentenyl Acetate Combined with Subsequent Enantioselective Crystallization

The recombinant pig liver esterase catalyzed hydrolysis of cis-1,4-diacetoxy-2-cyclopentene forming (1S,4R)-4-hydroxy-2-cyclopentenyl acetate was investigated and realized at preparative scale. Relevant reaction conditions were examined and optimized to achieve full conversion with an enantiomeric excess of about 86% ee. Enantiopure product was then obtained after enantioselective crystallization, which required further studies of the solid phase behavior, including its binary melting point phase diagram.