Hydrogen Bromide → HCID 66732491, compound

HRID 1963610Notes

Reaction equation

HRID 1963610 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:3]=1[CH2:4][C@H:5]1[CH2:10][C@H:9]([C:11]2[O:15][NH:14][C:13](=[O:16])[CH:12]=2)[CH2:8][CH2:7][N:6]1C(OC)=O.Br>>[F:1][C:2]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:3]=1[CH2:4][C@H:5]1[CH2:10][C@H:9]([C:11]2[O:15][NH:14][C:13](=[O:16])[CH:12]=2)[CH2:8][CH2:7][NH:6]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730484HCID 131730484, compound

Product 1

HCID 66732491HCID 66732491, compoundYield 44.3%

Procedure

Trans-methyl 2-(2,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (148 mg, 0.42 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 3 mL, 17.13 mmol) and the solution stirred at room temperature overnight. The solvent was evaporated and the residue was 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-(2,5-difluorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (54.7 mg, 44%). 1H NMR (400 MHz, cd3od) δ 1.90-2.00 (m, 1H), 2.10-2.25 (m, 3H), 3.05 (d, 2H), 3.09-3.19 (m, 1H), 3.34-3.45 (m, 2H), 3.51-3.61 (m, 1H), 5.81 (d, 1H), 7.02-7.21 (m, 3H). HRMS Calculated for [C15H16F2N2O2+H]+: 295.1258. Found: 295.1278

Workup

  1. customThe solvent was evaporated
  2. customthe residue was 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-81c8ab09c957457a93fafdbad5a373e7
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…