Hydrogen Bromide → HCID 46938210, compound

HRID 1963371Notes

Reaction equation

HRID 1963371 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

3

Reactant 2

HCID 260Hydrogen BromideHCID 66732221HCID 66732221, compound

Product 1

HCID 46938210HCID 46938210, compoundYield 52.2%

Procedure

(2S,4R)-Methyl 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.458 g, 1.36 mmol) (from example 27, step 3) was dissolved in hydrogen bromide (33% in acetic acid, 10.72 mL, 61.20 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-((2S,4R)-2-(4-chloro-phenyl)piperidin-4-yl)isoxazol-3(2H)-one (198 mg, 52%). 1H NMR (600 MHz, dmso) δ 1.32 (q, 1H), 1.44 (dq, 1H), 1.83-1.88 (m, 1H), 1.91-1.96 (m, 1H), 2.71 (dt, 1H), 2.84 (tt, 1H), 3.07-3.11 (m, 1H), 3.63 (dd, 1H), 5.70 (s, 1H), 7.31-7.40 (m, 4H). HRMS Calculated for [C14H15ClN2O2+H]+: 279.0900. Found: 279.0887

Workup

  1. customThe solvent was evaporated
  2. 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-625e4f209395420b9d9aacc69d3f62d2
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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