Hydrogen Bromide → HCID 66732573, compound

HRID 1963373Notes

Reaction equation

[Cl: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>>[Cl: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

Reactant 2

HCID 260Hydrogen Bromide

HCID 131730386HCID 131730386, compound

Product 1

HCID 66732573HCID 66732573, compoundYield 18.3%

Procedure

Trans-methyl 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (155 mg, 0.46 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 3.63 mL, 20.71 mmol) and the mixture was stirred at room temperature overnight. The solvent was evaporated 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-(trans-2-(4-chlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (23.5 mg, 18%). 1H NMR (600 MHz, dmso) δ 1.74-1.83 (m, 2H), 1.84-1.91 (m, 1H), 1.96-2.03 (m, 1H), 2.70 (dt, 1H), 2.79-2.86 (m, 1H), 3.09-3.15 (m, 1H), 3.69 (dd, 1H), 5.89-5.98 (m, 1H), 7.32-7.36 (m, 2H), 7.36-7.41 (m, 2H). HRMS Calculated for [C14H15ClN2O2+H]+: 279.0900. Found: 279.0889

Workup

customThe solvent was evaporated
customthe 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)

Sources & evidence

ORD record: ord-9253e7e3a0c042d28aeb5c9886ed1cfd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415378B2

Reaction notes

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