Hydrogen Bromide → HCID 66732456, compound

HRID 1963366Notes

Reaction equation

HRID 1963366 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][C@H:12]([C:14]3[O:18][NH:17][C:16](=[O:19])[CH:15]=3)[CH2:11][CH2:10][N:9]2C(OC)=O)=[CH:4][CH:3]=1.Br>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][C@H:12]([C:14]3[O:18][NH:17][C:16](=[O:19])[CH:15]=3)[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730383HCID 131730383, compound

Product 1

HCID 66732456HCID 66732456, compound

Procedure

Trans-methyl 2-(4-fluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.3 g, 0.94 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 6 mL, 34.26 mmol) and the solution stirred at room temperature overnight. The solvent was evaporated and the residue was purified by preparative HPLC (Instrument: Agilent, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) 5-(Trans-2-(4-fluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (54 mg, 22%) was isolated. 1H NMR (400 MHz, dmso) δ 1.75-2.10 (m, 4H), 2.67-2.77 (m, 1H), 2.80-2.89 (m, 1H), 3.11-3.18 (m, 1H), 3.70 (d, 1H), 5.94 (s, 1H), 7.07-7.15 (m, 2H), 7.36-7.43 (m, 2H). HRMS Calculated for [C14H15FN2O2+H]+: 263.1196. Found: 263.1201

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC (Instrument: Agilent, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) 5-(Trans-2-(4-fluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (54 mg, 22%)
  3. customwas isolated

Sources & evidence

ORD record
ord-f0649edf59844e61925a5fe9a653f9aa
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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