Hydrogen Bromide → HCID 66732314, compound

Participants

Reaction Steps

(2S,4R)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3,4,5-trifluorobenzyl)piperidine-1-carboxylate (598 mg, 1.61 mmol) (from example 143, step 3) was dissolved in hydrogen bromide (33% in AcOH, 7 mL, 99.92 mmol) and stirred at room temperature for 20 h. The solvent was evaporated in vacuo and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2S,4R)-2-(3,4,5-trifluorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (357 mg, 70.8%). 1H NMR (600 MHz, dmso) δ 1.05 (q, 1H), 1.32 (dq, 1H), 1.70-1.78 (m, 2H), 2.33-3.58 (m, 6H), 5.68 (s, 1H), 7.12-7.19 (m, 2H). HRMS Calculated for [C15H15F3N2O2+H]+: 313.1164. Found: 313.1158

Provenance & Evidence