Isopropanol heptane → HCID 68505870, compound

Participants

Reaction Steps

Cis-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)phenyl)piperidine-1-carboxylate (311 mg, 0.84 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak IC (250×20), 5 μm particle size, mobile phase: Heptane/IPA 40/60, flow rate 12 mL/min) to yield (2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)-phenyl)piperidine-1-carboxylate (155 mg, 50%), Chiral purity 99.9% ee, Optical rotation [α]D20=−54.4 (acetonitrile, c=1), 1H NMR (400 MHz, cdcl3) δ 1.78-1.90 (m, 1H), 2.08-2.42 (m, 3H), 3.01-3.13 (m, 1H), 3.34-3.48 (m, 1H), 3.65 (s, 3H), 4.09-4.22 (m, 1H), 5.08-5.19 (m, 1H), 5.53 (s, 1H), 7.31-7.50 (m, 4H) and (2S,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)phenyl)piperidine-1-carboxylate (152 mg, 49%), Chiral purity 99.9% ee. Optical rotation [α]D20=−55.7 (acetonitrile, c=1), 1H NMR (400 MHz, cdcl3) δ 1.80-1.90 (m, 1H), 2.11-2.32 (m, 2H), 2.33-2.42 (m, 1H), 3.02-3.12 (m, 1H), 3.36-3.47 (m, 1H), 3.66 (s, 3H), 4.12-4.21 (m, 1H), 5.11-5.17 (m, 1H), 5.53 (s, 1H), 7.33-7.48 (m, 4H).

Provenance & Evidence