Acetic Acid → HCID 66732300, compound

HRID 1963656Notes

Reaction equation

HRID 1963656 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=1)[CH2:8][C@H:9]1[CH2:14][C@@H:13]([C:15]2[O:19][NH:18][C:17](=[O:20])[CH:16]=2)[CH2:12][CH2:11][N:10]1C(OC)=O)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>Br>[C:28]([C:26]1[CH:25]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:27]=1)[CH2:8][C@H:9]1[CH2:14][C@@H:13]([C:15]2[O:19][NH:18][C:17](=[O:20])[CH:16]=2)[CH2:12][CH2:11][NH:10]1)([CH3:30])([CH3:31])[CH3:29]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 68501980HCID 68501980, compound

Product 1

HCID 66732300HCID 66732300, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

(2R,4S)-Methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (550 mg, 1.28 mmol) was dissolved in hydrogen bromide (33% in acetic acid (10 mL, 57.10 mmol) and the mixture stirred at room temperature overnight. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx III, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-(3,5-di-tert-butylbenzyl)piperidin-4-yl)isoxazol-3(2H)-one (315 mg, 66%). 1H NMR (600 MHz, cd3od) δ 1.30 (s, 18H), 1.58-1.67 (m, 1H), 1.80 (dq, 1H), 2.17-2.27 (m, 2H), 2.85-3.14 (m, 4H), 3.41-3.51 (m, 2H), 5.73 (s, 1H), 7.07-7.13 (m, 2H), 7.36-7.40 (m, 1H). HRMS Calculated for [C23H34N2O2+H]+: 371.2698. Found: 371.2714

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx III, 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-7ded545fedb440f8bfc80e8870680610
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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