Convenient enzymatic resolution of cis-6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione using lipase to prepare the intermediate of moxifloxacin.

A convenient and efficient route has been successfully developed for preparing (4a R ,7a S )-6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione through enzyme-mediated kinetic resolution processes under mild and environmentally acceptable conditions. Different reaction condition factors, including acyl agent, solvent, reaction temperature, and the concentration of Et 3 N, were optimized in order to establish the optimal reaction conditions for the enzymatic kinetic resolution of secondary amines. It was demonstrated that acyl agent, the concentration of Et 3 N or the type of solvent have a greater influence on the selectivity and rate of the asymmetric acylation reaction in the process of the enzymatic resolution, respectively. The target product amine was obtained in good conversion (49%) and an excellent degree of enantiomeric purity (>99%) when Candida antarctica lipase B (CAL-B) and phenyl allyl carbonates were combined to use in the tert-butyl methyl ether (TBME) medium. This method will be an alternative to the traditional route for producing the optically pure intermediate of moxifloxacin. [ABSTRACT FROM AUTHOR]