Ethanol heptane → HCID 68499998, compound

Participants

Reaction Steps

Cis-Methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (1.47 g, 3.66 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 90/10, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (703 mg, 47.8%), Chiral purity 99.3% ee, Optical rotation [α]D20=+5.5 (acetonitrile, c=1) and (2S,4R)-methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (675 mg, 45.9%), Chiral purity 99.7% ee, Optical rotation [α]D20=−5.1 (acetonitrile, c=1)

Provenance & Evidence