Isopropanol heptane → HCID 66734831, compound

Participants

Reaction Steps

Cis-methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (1.32 g, 3.28 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 85/15, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (594 mg, 46%), Chiral purity 99.5% ee, Optical rotation [α]D20=+9.1 (acetonitrile, c=1) and (2S,4R)-methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (589 mg, 45%), Chiral purity 99.2% ee, Optical rotation [α]D20=−8.8 (acetonitrile, c=1)

Provenance & Evidence