Water → Rac-2-chloro-4-[(4r,5s)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrile

HRID 1173687노트

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HRID 1173687 반응식
[Si]([O:8][C@H:9]1[C@H:13]([CH3:14])[N:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([Cl:23])[C:16]=2[CH3:24])[C:11](=[O:25])[C:10]1([CH3:27])[CH3:26])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[Cl:23][C:17]1[C:16]([CH3:24])=[C:15]([N:12]2[C@@H:13]([CH3:14])[C@H:9]([OH:8])[C:10]([CH3:27])([CH3:26])[C:11]2=[O:25])[CH:22]=[CH:21][C:18]=1[C:19]#[N:20]

참가 물질

5

반응물 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 59556867Rac-4-((4r,5s)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl)-2-chloro-3-methylbenzonitrile

생성물 1

HCID 59556873Rac-2-chloro-4-[(4r,5s)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrile수율 55.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of rac-4-[(4R,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-2-chloro-3-methylbenzonitrile (103 mg) in THF (5 mL) was added tetrabutylammonium fluoride-THF solution (1.00 mL, 1 mol/L), and the mixture was stirred at room temperature for 17 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/3), and recrystallized from hexane-ethyl acetate to give the title compound as a colorless solid (yield: 41.4 mg, 28.4%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/3)
  6. customrecrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-a38983109f6b447d86a5296256103640
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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