Methanol → (2S,4R)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)phenyl)piperidine-1-carboxylate

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Reaction Steps

Cis-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)phenyl)piperidine-1-carboxylate (1.682 g, 4.54 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak IA (250×30), 5 μm particle size, mobile phase: 15% MeOH in CO2 (175 bar), flow rate 130 mL/min, temperature 40° C.) to yield (2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)phenyl)piperidine-1-carboxylate (580 mg, 34%), Chiral purity 99.9% ee, Optical rotation [α]D20=+53.3 (acetonitrile, c=1) and (2S,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)phenyl)piperidine-1-carboxylate (591 mg, 35%), Chiral purity 98.8% ee, Optical rotation [α]D20=−74.2 (acetonitrile, c=1)

Provenance & Evidence