Hydrogen Bromide → HCID 66732264, compound

HRID 1963635Notes

Reaction equation

HRID 1963635 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1C(OC)=O.Br>>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][NH:7]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 68499998HCID 68499998, compound

Product 1

HCID 66732264HCID 66732264, compoundYield 62.2%

Procedure

(2R,4S)-Methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.703 g, 1.75 mmol) was dissolved in hydrogen bromide (33% in AcOH, 5 mL, 71.37 mmol) and stirred at room temperature overnight. The solvents were evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-(3-fluoro-5-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (375 mg, 62%). 1H NMR (600 MHz, dmso) δ 1.08 (q, 1H), 1.31 (dq, 1H), 1.71-1.80 (m, 2H), 2.48-2.54 (m, 1H), 2.63-2.80 (m, 4H), 2.92-2.99 (m, 1H), 5.65 (s, 1H), 7.37-7.46 (m, 3H). HRMS Calculated for [C16H16F4N2O2+H]+: 345.1226. Found: 345.1228

Workup

  1. customThe solvents were evaporated
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm)

Sources & evidence

ORD record
ord-fcc62e6b89824f58ba25fca01103ca4e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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