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

HRID 882515Notes

Reaction equation

HRID 882515 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-].[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 23665763Sodium BisulfiteHCID 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 bisulfite 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-213ed0d23442472e9c08cfcccbd80b94
Source dataset
uspto-grants-2015_03
Patent number
US08993785B2

Reaction notes

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