Hydrogen Bromide → HCID 66732176, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (619 mg, 1.44 mmol) (from example 146, step 3) was dissolved in hydrogen bromide (33% in acetic acid, 10 mL, 57.10 mmol) and the mixture stirred at room temperature overnight. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx III, 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-(3,5-di-tert-butylbenzyl)piperidin-4-yl)isoxazol-3(2H)-one (330 mg, 61%). 1H NMR (600 MHz, cd3od) δ 1.30 (s, 18H), 1.63 (q, 1H), 1.80 (dq, 1H), 2.19-2.27 (m, 2H), 2.86-3.18 (m, 4H), 3.43-3.56 (m, 2H), 5.73 (s, 1H), 7.10 (d, 2H), 7.37-7.40 (m, 1H). HRMS Calculated for [C23H34N2O2+H]+: 371.2698. Found: 371.2693

Provenance & Evidence