Ethanol heptane → HCID 66732293, compound

Participants

Reaction Steps

Cis-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.604 g, 4.56 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 90/10, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (645 mg, 40%), Chiral purity 99.2% ee, Optical rotation [α]D20=+13.1 (MeOH, c=1) and (2S,4R)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (789 mg, 49%), Chiral purity 99.6% ee, Optical rotation [α]D20=−10.1 (MeOH, c=1)

Provenance & Evidence