Isopropanol heptane → HCID 66742254, compound

Participants

Reaction Steps

Cis-methyl 2-((4,4-difluorocyclohexyl)methyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.6 g, 4.46 mmol) was subjected to chiral preparative HPLC (Column: CelluCoat (250×20), 5 μm particle size, mobile phase: Heptane/IPA 80/20, flow rate 18 mL/min) to yield (2S,4S)-methyl 2-((4,4-difluorocyclohexyl)methyl)-4-(3-oxo-2,3-dihydro-isoxazol-5-yl)piperidine-1-carboxylate (787 mg, 49%), Chiral purity 99.8% ee, Optical rotation [α]D20=+28.8 (acetonitrile, c=1) and (2R,4R)-methyl 2-((4,4-difluorocyclohexyl)-methyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (752 mg, 47%) Chiral purity 99.9% ee, Optical rotation [α]D20=−30.2 (acetonitrile, c=1).

Provenance & Evidence