Hydrogen Peroxide → HCID 44194661, compound

HRID 1192937Notes

Reaction equation

HRID 1192937 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([CH3:27])([CH3:26])[C:24]#[N:25])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][C:11]2=[O:28])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=[O:30].[K+].[K+].OO>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([CH3:27])([CH3:26])[C:24]([NH2:25])=[O:30])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][C:11]2=[O:28])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 44194660HCID 44194660, compound

Product 1

HCID 44194661HCID 44194661, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 3-((S)-1-((S)-1-(4-bromophenyl)ethyl)-2-oxo-4-phenylpiperidin-4-yl)-2,2-dimethylpropanenitrile (11 mg, 0.025 mmol) in DMSO (3 mL) were added K2CO3 (6.9 mg 0.05 mmol) and 30% H2O2 (5.7 mg 0.05 mmol). The mixture was stirred at rt overnight. After being diluted with water (2 mL), the mixture was washed with EtOAc (3×2 mL). The aqueous layer was acidified to pH=3-4, and extracted with EtOAc (3×2 mL). The combined organic layers were washed with brine (3×2 mL), dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The crude product was dried under vacuum and purified by TLC and preparative HPLC to give 3-((S)-1-((S)-1-(4-bromophenyl)ethyl)-2-oxo-4-phenylpiperidin-4-yl)-2,2-dimethylpropanamide (8 mg, 70%). LC-MS Method 2 tR=1.36 min, m/z=481, 479, 459, 457; 1H NMR (CDCl3): δ 0.78 (s, 3H), 1.08 (s, 3H), 1.40 (d, 3H), 2.0 (m, 4H), 2.18 (m, 1H), 2.66 (m, 1H), 2.81 (m, 1H), 3.32 (m, 1H), 5.58 (m, 1H), 5.84 (m, 1H), 6.18 (m, 1H), 6.68 (m, 2H), 7.16 (m, 2H), 7.20 (m, 5H).

Workup

  1. washthe mixture was washed with EtOAc (3×2 mL)
  2. extractionextracted with EtOAc (3×2 mL)
  3. washThe combined organic layers were washed with brine (3×2 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. dry with materialThe crude product was dried under vacuum
  8. custompurified by TLC and preparative HPLC

Sources & evidence

ORD record
ord-e6d3fda66eb046f7b6225f31956652d9
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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