Ethanol heptane → HCID 66732566, compound

Participants

Reaction Steps

Cis-methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.358 g, 3.16 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×20), 5 μm particle size, mobile phase: Heptane/EtOH/FA 90/10/0.1, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (550 mg, 40%), Chiral purity 99.6% ee, Optical rotation [α]D20=+14.7 (acetonitrile, c=1) and (2S,4R)-methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (619 mg, 45%), Chiral purity 99.7% ee, Optical rotation [α]D20=−11.2 (acetonitrile, c=1)

Provenance & Evidence