Tetrabutylammonium Fluoride → HCID 57743036, compound

HRID 1896371Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[C:5]([CH3:23])[N:4](S(C2C=CC(C)=CC=2)(=O)=O)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[C:5]([CH3:23])[NH:4][N:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In a 100 ml flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, 1-({3,5-dimethyl-1-[(4-methyl phenyl)sulfonyl]-1H-pyrazol-4-yl}methyl)-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one x61 (0.83 g, 1.7 mmol) is dissolved in THF (40 ml). A 1 M solution of tetrabutylammonium fluoride in THF (1.7 ml, 1.7 mmol) is added and the mixture is heated at 85° C. for 48 h. The solvent is evaporated and the residue is dissolved in water. The aqueous phase is extracted six times with diethylether and the combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. The crude product is purified by preparative chromatography on silicagel and recrystallized from AcOEt to give 77 mg of 1-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 167.

Workup

customThe solvent is evaporated
dissolutionthe residue is dissolved in water
extractionThe aqueous phase is extracted six times with diethylether
dry with materialthe combined organic phases are dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product is purified by preparative chromatography on silicagel
customrecrystallized from AcOEt

Sources & evidence

ORD record: ord-500badaf0e0f42be83cefdbc60844177
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518943B2

Reaction notes

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