Isopropanol heptane → (2S,4R)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)benzyl)piperidine-1-carboxylate

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Reaction Steps

Cis-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)benzyl)piperidine-1-carboxylate (1.27 g, 3.31 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/IPA/FA 90/10/0.1, flow rate 18 mL/min) to yield (2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)benzyl)piperidine-1-carboxylate (620 mg, 49%), Chiral purity 99.7% ee, Optical rotation [α]D20=+7.3 (acetonitrile, c=1) and (2S,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)benzyl)piperidine-1-carboxylate (640 mg, 50%), Chiral purity 99.3% ee, Optical rotation [α]D20=−6.3 (acetonitrile, c=1)

Provenance & Evidence