Isopropanol heptane → HCID 68500328, compound

Participants

Reaction Steps

Trans-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.648 g, 1.84 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 70/30, flow rate 18 mL/min) to yield (2S,4S)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate 249 mg (38%), Chiral purity 99.9% ee, Optical rotation [α]D20=+27.1 (acetonitrile, c=1) and (2R,4R)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (244 mg, 37%), Chiral purity 99.9% ee, Optical rotation [α]D20=−26.4 (acetonitrile, c=1)

Provenance & Evidence