Hydrogen Bromide → HCID 46938266, compound

HRID 1963396Notes

Reaction equation

HRID 1963396 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C@@H:15]([C:17]3[O:21][NH:20][C:19](=[O:22])[CH:18]=3)[CH2:14][CH2:13][N:12]2C(OC)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C@@H:15]([C:17]3[O:21][NH:20][C:19](=[O:22])[CH:18]=3)[CH2:14][CH2:13][NH:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 66741776HCID 66741776, compound

Product 1

HCID 46938266HCID 46938266, compoundYield 68%

Procedure

(2R,4S)-Methyl 2-(4-(methylsulfonyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (536 mg, 1.41 mmol) was dissolved in hydrogen bromide (33% in AcOH, 5 mL, 71.37 mmol) and stirred at room temperature for 20 h. The reaction mixture was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx III, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-(4-(methylsulfonyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (309 mg, 68%), 1H NMR (600 MHz, dmso) δ 1.39 (q, 1H), 1.49 (dq, 1H), 1.87-1.93 (m, 1H), 2.01 (d, 1H), 2.76 (t, 1H), 2.87-2.94 (m, 1H), 3.11-3.19 (m, 1H), 3.17 (s, 3H), 3.80 (d, 1H), 5.74 (s, 1H), 7.64 (d, 2H), 7.85 (d, 2H). HRMS Calcd for [C15H18N2O4S+H]+: 323.1065. Found: 323.1042.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx III, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm)

Sources & evidence

ORD record
ord-6e9c9e8f1d6a4cc5bd45ab0e179a7c86
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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