Chemo-enzymatic synthesis of both enantiomers of the anti-anginal drug ranolazine

Both enantiomers of the potential anti-anginal drug ranolazine have been synthesized from enantiopure (R)- and (S)-3-chloro-1-(2-methoxyphenoxy)propan-2-ol. These chiral building blocks were produced by kinetic resolution of the corresponding racemic butanoate by hydrolysis catalyzed by immobilized lipase from Rhizomucor miehei (Lipozym RM IM) or lipase B from Candida antarctica (Novozym 435). (R)-3-Chloro-1-(2-methoxyphenoxy)propan-2-ol was also made from the racemate in high yield and ee in a stereoinversion reaction.