Hydrogen Bromide → 5-(trans-2-(4-Tert-butylphenyl)piperidin-4-yl)isoxazol-3(2h)-one

HRID 1963393Notes

Reaction equation

HRID 1963393 reaction equation
[C:1]([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)([CH3:4])([CH3:3])[CH3:2].Br>>[C:1]([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)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730394HCID 131730394, compound

Product 1

HCID 667321645-(trans-2-(4-Tert-butylphenyl)piperidin-4-yl)isoxazol-3(2h)-oneYield 84%

Procedure

Trans-methyl 2-(4-tert-butylphenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.26 g, 0.73 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 5 mL, 71.37 mmol) and stirred at room temperature for 18 h. Solvents were 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-(trans-2-(4-tert-butylphenyl)piperidin-4-yl)isoxazol-3(2H)-one (182 mg, 84%). 1H NMR (600 MHz, dmso) δ 1.23 (s, 9H), 1.76-1.85 (m, 2H), 1.86-1.93 (m, 1H), 1.96-2.03 (m, 1H), 2.71 (td, 1H), 2.81-2.88 (m, 1H), 3.10-3.15 (m, 1H), 3.65 (dd, 1H), 5.90 (s, 1H), 7.24-7.33 (m, 4H). HRMS Calculated for [C18H24N2O2+H]+: 301.1916. Found: 301.1919

Workup

  1. customSolvents were 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-1817e36b40be4734ba946f3be0b118fe
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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