Ethanol → HCID 66732221, compound

Participants

Reaction Steps

Cis-methyl 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (923 mg, 2.75 mmol) was subjected to chiral preparative HPLC (Column: ReproSil (250×50), 8 μm particle size, mobile phase: EtOH, flow rate 100 mL/min) to yield (2R,4S)-methyl 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (447 mg, 48%), Chiral purity 99.9% ee, Optical rotation [α]D20=+67.7 (acetonitrile, c=1), 1H NMR (400 MHz, cdcl3) δ 1.79-1.89 (m, 1H), 2.07-2.40 (m, 3H), 3.01-3.11 (m, 1H), 3.33-3.43 (m, 1H), 3.66 (s, 3H), 4.10-4.19 (m, 1H), 5.07 (dd, 1H), 5.55 (s, 1H), 7.08-7.14 (m, 2H), 7.23-7.28 (m, 2H) and (2S,4R)-methyl 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (458 mg, 49%), Chiral purity 99.6% ee, Optical rotation [α]D20=−67.6 (acetonitrile, c=1), 1H NMR (400 MHz, cdcl3) δ 1.79-1.88 (m, 1H), 2.07-2.38 (m, 3H), 3.02-3.10 (m, 1H), 3.33-3.43 (m, 1H), 3.66 (s, 3H), 4.11-4.18 (m, 1H), 5.04-5.09 (m, 1H), 5.54 (s, 1H), 7.09-7.13 (m, 2H), 7.23-7.28 (m, 2H).

Provenance & Evidence