Hydrogen Bromide → HCID 46937760, compound

HRID 1963563Notes

Reaction equation

HRID 1963563 reaction equation
Br.[O:2]=[C:3]1[CH:7]=[C:6]([C@H:8]2[CH2:13][CH2:12][N:11](C(OC)=O)[C@H:10]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[CH2:9]2)[O:5][NH:4]1>>[F:28][C:25]([F:26])([F:27])[C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C@@H:10]2[CH2:9][C@@H:8]([C:6]3[O:5][NH:4][C:3](=[O:2])[CH:7]=3)[CH2:13][CH2:12][NH:11]2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 66734963HCID 66734963, compound

Product 1

HCID 46937760HCID 46937760, compoundYield 76.6%

Procedure

Hydrogen bromide (33% in acetic acid, 5 mL) was added to a reaction flask containing (2S,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (77 mg, 0.20 mmol). The reaction was stirred vigorously overnight. The solvent was evaporated. Purification using PrepLC (pH=11, small column, sample dissolved in MeOH, gradient 5-45, 20 min) yielded 5-((2S,4S)-2-(4-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (50 mg, 76%). 1H NMR (600 MHz, cd3od) δ 1.73-1.79 (m, 1H), 1.98-2.12 (m, 3H), 2.93 (dd, 1H), 2.97-3.04 (m, 2H), 3.17-3.25 (m, 2H), 3.35-3.41 (m, 1H), 5.48 (s, 1H), 7.41 (d, 2H), 7.61 (d, 2H). HRMS Calcd for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1289.

Workup

  1. customThe solvent was evaporated
  2. customPurification
  3. dissolutionPrepLC (pH=11, small column, sample dissolved in MeOH, gradient 5-45, 20 min)

Sources & evidence

ORD record
ord-ccf603b3fd40499d8bc22923a9b07f4e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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