(3S,3aR,6aR)-5,5-difluoro-3-fluoromethyl-3-(2-fluoro-phenyl)-hexahydro-cyclopenta[d]isoxazole → (3R,3aS,6aS)-5,5-difluoro-3-fluoromethyl-3-(2-fluoro-phenyl)-hexahydro-cyclopenta[d]isoxazole

Participants

Reaction Steps

Intermediate XXII-1: The racemate of (3S,3aR,6aR)-5,5-difluoro-3-fluoromethyl-3-(2-fluoro-phenyl)-hexahydro-cyclopenta[d]isoxazole was resolved on a chiral high-performance liquid chromatography (HPLC) column (Chiralpak AD) using n-heptane/ethanol (85:15) to give (3R,3aS,6aS)-5,5-difluoro-3-fluoromethyl-3-(2-fluoro-phenyl)-hexahydro-cyclopenta[d]isoxazole as the faster eluting enantiomer and the desired (3S,3aR,6aR)-5,5-difluoro-3-fluoromethyl-3-(2-fluoro-phenyl)-hexahydro-cyclopenta[d]isoxazole as the slower eluting enantiomer. MS: m/z=276.1 [M+H]+.

Provenance & Evidence