Ethanol heptane → HCID 68500258, compound

Participants

Reaction Steps

Cis-methyl 2-(2,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.259 g, 3.58 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH/FA 90/10/0.2, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(2,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (505 mg, 40%), Chiral purity 98.8% ee, Optical rotation [α]D20=−5.7 (acetonitrile, c=1) and (2S,4R)-methyl 2-(2,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (499 mg, 39.6%), Chiral purity 98.8% ee, Optical rotation [α]D20 +3.5 (acetonitrile, c=1).

Provenance & Evidence