Hydrogen Peroxide → 3-[4-(3-Benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide

HRID 1819349Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][N:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]#[N:24])[C:17](=[O:28])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:29].[Na+].OO>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][N:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]([NH2:24])=[O:29])[C:17](=[O:28])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 3-[4-(3-benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile (1.3 g, 3.36 mmol) in 25 mL EtOH was added 25% NaOH (0.15 mL) followed by the slow addition of 1.5 mL H2O2 (30%). The reaction mixture was heated to 45° C. and stirred for 5 h. The mixture was then cooled down and concentrated under reduced pressure. The residue was dissolved in 100 mL EtOAc, washed with water and brine, dried over MgSO4 and concentrated again. The residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3) to give 1.3 g of the desired product. Yield: 99%.

Workup

temperatureThe mixture was then cooled down
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in 100 mL EtOAc
washwashed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated again
customThe residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3)

Sources & evidence

ORD record: ord-16229d3feaf9405aafdf90f967208192
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601742B2

Reaction notes

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