Hydrogen Bromide → HCID 46937761, compound

HRID 1963564Notes

Reaction equation

HRID 1963564 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 68500325HCID 68500325, compound

Product 1

HCID 46937761HCID 46937761, compoundYield 65%

Procedure

Hydrogen bromide (33% in acetic acid, 5 mL) was added to a reaction flask containing (2R,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (87 mg, 0.23 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-((2R,4R)-2-(4-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (48 mg, 65%). 1H NMR (600 MHz, cd3od) δ 1.74-1.80 (m, 1H), 1.99-2.13 (m, 3H), 2.94 (dd, 1H), 2.98-3.05 (m, 2H), 3.19-3.26 (m, 2H), 3.36-3.42 (m, 1H), 5.50 (s, 1H), 7.42 (d, 2H), 7.62 (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-55899e9186ce4e479d56d1fa7d13592f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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