Abstract
A convenient and efficient route has been successfully developed for preparing (4aR,7aS)-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 Et3N, 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 Et3N 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.
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