Hydrogen Peroxide → 1-ethyl-7-[5-hydroxymethyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one

HRID 1869556Notes

Reaction equation

HRID 1869556 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH3:27])=[C:10]([C:13]3[CH:18]=[C:17]([CH:19]=C)[CH:16]=[CH:15][C:14]=3[O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:11]=2)[C:6]([CH3:29])([CH3:28])[CH2:5][C:4]1=[O:30])[CH3:2].CSC.B.[OH-:35].[Na+].OO>C1COCC1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH3:27])=[C:10]([C:13]3[CH:18]=[C:17]([CH2:19][OH:35])[CH:16]=[CH:15][C:14]=3[O:21][CH2:22][C:23]([F:24])([F:25])[F:26])[CH:11]=2)[C:6]([CH3:28])([CH3:29])[CH2:5][C:4]1=[O:30])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 579863101-ethyl-4,4,6-trimethyl-7-[2-(2,2,2-trifluoro-ethoxy)-5-vinyl-phenyl]-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 686666991-ethyl-7-[5-hydroxymethyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Compound 55A (0.24 mmol, 0.1 g) in 2 mL THF was added a solution of borane dimethylsulfide in THF (0.36 mmol, 0.03 mL) at 0° C. and the reaction mixture was stirred overnight. A solution of 2M NaOH (1 mL) was then added followed by a dropwise addition of hydrogen peroxide (30%, 1 mL). The solution was stirred at r.t. for 3 h. It was extracted with EtOAc, washed with water and brine, dried over Na2SO4, filtered and concentrated. The LCMS indicated the presence of the desired product (m/z found 436) and a byproduct where the amide carbonyl group was reduced to a methylene group (m/z found 422). The residue was purified by column chromatography (3:1 hexane/EtOAc followed by 1:1 hexane/EtOAc) to obtain 1-ethyl-7-[5-hydroxymethyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one as a colorless oil (0.073 g).

Workup

  1. stirringThe solution was stirred at r.t. for 3 h
  2. extractionIt was extracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (3:1 hexane/EtOAc followed by 1:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-35e00f07260e44b69b0c29de2f2d440b
Source dataset
uspto-grants-2009_12
Patent number
US07638533B2

Reaction notes

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