Hydrogen Bromide → HCID 66731893, compound

HRID 1963619Notes

Reaction equation

HRID 1963619 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([F:25])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1C(OC)=O.Br>>[F:25][C:23]1[CH:22]=[C:4]([CH:3]=[C:2]([F:1])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][NH:7]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 68500326HCID 68500326, compound

Product 1

HCID 66731893HCID 66731893, compoundYield 28.4%

Procedure

(2R,4S)-Methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.645 g, 1.83 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 14.43 mL, 82.38 mmol) and the mixture was stirred at room temperature overnight. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx III, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-(3,5-difluorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (153 mg, 28%). 1H NMR (600 MHz, dmso) δ 1.01-1.11 (m, 1H), 1.26-1.38 (m, 1H), 1.68-1.78 (m, 2H), 2.41-2.77 (m, 5H), 2.91-2.99 (m, 1H), 5.67 (s, 1H), 6.92 (d, 2H), 6.99 (s, 1H). HRMS Calculated for [C15H16F2N2O2+H]+: 295.1258. Found: 295.1249

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx III, 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-b0344c59c2fd4e5d90529184a976ee81
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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