Hydrogen Bromide → HCID 66732651, compound

HRID 1963438Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2C(OC)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br>>[Cl:8][C:6]1[CH:5]=[C:4]([C@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][NH:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 131730412HCID 131730412, compound

Product 1

HCID 66732651HCID 66732651, compoundYield 64%

Procedure

Trans-methyl 2-(3,5-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (300 mg, 0.81 mmol) was diluted with hydrogen bromide (33% in AcOH, 4.3 mL, 24.24 mmol) and stirred at ambient temperature for 48 h. 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-(3,5-dichlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (162 mg, 64%). 1H NMR (600 MHz, CDCl3) δ 1.77-2.17 (m, 4H), 2.66-2.74 (m, 1H), 2.82-2.89 (m, 1H), 3.12-3.18 (m, 1H), 3.79 (d, 1H), 6.06 (s, 1H), 7.44-7.51 (m, 3H). HRMS Calculated for [C14H14Cl2N2O2+H]+: 313.0511. Found: 313.0513

Workup

customEvaporated
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-19063297f0af4803b781464af94fcd02
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415378B2

Reaction notes

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