Hydrogen Bromide → HCID 66732863, compound

HRID 1963582Notes

Reaction equation

HRID 1963582 reaction equation
[O:1]=[C:2]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][N:10](C(OC)=O)[C@@H:9]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:8]2)[O:4][NH:3]1.Br>>[F:28][C:25]([F:26])([F:27])[O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C@H:9]2[CH2:8][C@H:7]([C:5]3[O:4][NH:3][C:2](=[O:1])[CH:6]=3)[CH2:12][CH2:11][NH:10]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730475HCID 131730475, compound

Product 1

HCID 66732863HCID 66732863, compoundYield 38.8%

Procedure

Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethoxy)benzyl)piperidine-1-carboxylate (0.603 g, 1.51 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 11.87 mL, 67.78 mmol) and the mixture was stirred at room temperature overnight. The solvent was evaporated and the compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm) using a gradient of 10-50% Acetonitrile in H2O/AcN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 100 mL/min. 5-(Trans-2-(4-(trifluoromethoxy)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (200 mg, 38.8%) was isolated as a white solid. 1H NMR (400 MHz, dmso) δ 1.47-1.60 (m, 1H), 1.68-1.87 (m, 3H), 2.43-4.01 (m, 6H), 5.73 (s, 1H), 7.20-7.40 (m, 4H). HRMS Calculated for [C16H17F3N2O3+H]+: 343.1270. Found: 343.1260

Workup

  1. customThe solvent was evaporated
  2. customthe compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm)
  3. custombuffer over 20 minutes

Sources & evidence

ORD record
ord-22cf491c90244ca5889712c5edad89c3
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…