HCID 66732072, compound → HCID 66732117, compound

HRID 1963588Notes

Reaction equation

HRID 1963588 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2C(OC)=O)=[CH:4][CH:3]=1>Br>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C@H:7]2[CH2:12][C@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 66732072HCID 66732072, compound

Product 1

HCID 66732117HCID 66732117, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Methyl 2-(4-chlorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (347 mg, 0.99 mmol) was stirred in HBr (33% in AcOH) overnight (19 hours). Evaporation of solvents 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) yielded 5-(trans-2-(4-chlorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (151 mg, 52%). 1H NMR (400 MHz, tfa) δ 2.25-2.60 (m, 4H), 3.06-3.20 (m, 2H), 3.35-3.52 (m, 1H), 3.55-3.75 (s, 2H), 3.77-3.96 (m, 1H), 6.59 (s, 1H), 7.15-7.22 (m, 2H), 7.22-7.41 (m, 2H). HRMS Calcd for [C15H17ClN2O2+H]+: 293.1057. Found: 293.1031.

Workup

  1. customEvaporation of solvents
  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-d0413b6350ab48038c91af8e9c1eb413
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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