Tetrabutylammonium Fluoride → HCID 57743036, 화합물

HRID 2043594노트

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HRID 2043594 반응식
[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

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 53629161HCID 53629161, 화합물

생성물 1

HCID 57743036HCID 57743036, 화합물수율 14%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
85 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0e21301312d046e48f07d636468240fb
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586623B2

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