Hydrogen Peroxide → (r)-5-Biphenyl-4-ylmethyl-3,3-dimethylpyrrolidin-2-one

HRID 1641637Notes

Reaction equation

HRID 1641637 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]2[N:12](C(=O)C(C)(C)C)[C:11](=[O:19])[C:10]([CH3:21])([CH3:20])[CH2:9]2)=[CH:3][CH:2]=1.[OH-].[Li+].OO.S(=O)(=O)(O)[O-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[C:1]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]2[NH:12][C:11](=[O:19])[C:10]([CH3:21])([CH3:20])[CH2:9]2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 59318477(R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3,3-dimethyl-pyrrolidin-2-one

Product 1

HCID 59318449(r)-5-Biphenyl-4-ylmethyl-3,3-dimethylpyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

6 g (R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3,3-dimethyl-pyrrolidin-2-one is added to THF (6 ml). Lithium hydroxide (15.6 ml, 3 mol L−1) is added followed by tetra-butylammonium bromide (0.15 g). This mixture is then added to a mixture of hydrogen peroxide (4.54 g) and THF (12 ml) at 0° C. After 2.5 h, sodium bisulfate solution (12 g, 38-40%) is added. THF is removed in vacuo. Toluene (70 ml) is added and the phases separated. The organic phase is washed with water (15 ml). The phases are separated. The organic phase is concentrated in vacuo and then heptane (60 ml) is added and the mixture cooled to 0° C.). The precipitate is collected by filtration and dried in vacuo to give (R)-5-Biphenyl-4-ylmethyl-3,3-dimethylpyrrolidin-2-one 1H NMR (DMSO): 0.96 (3H), 0.97 (3H), 1.52 (1H), 1.78 (1H), 2.61 (1H), 2.93 (1H), 3.75 (1H), 7.32 (3H), 7.45 (2H), 7.58 (2H), 7.63 (2H), 7.70 (1H).

Workup

  1. customTHF is removed in vacuo
  2. additionToluene (70 ml) is added
  3. customthe phases separated
  4. washThe organic phase is washed with water (15 ml)
  5. customThe phases are separated
  6. concentrationThe organic phase is concentrated in vacuo
  7. additionheptane (60 ml) is added
  8. filtrationThe precipitate is collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-e4272e0c9b444b15a19316a9dea13ae9
Source dataset
uspto-grants-2012_02
Patent number
US08115016B2

Reaction notes

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