Water → benzyl (2S,3S)-3-hydroxy-2-methyl-3-(trifluoromethyl)pyrrolidine-1-carboxylate
반응식
[CH3:1][C@H:2]1[C:6](=[O:7])[CH2:5][CH2:4][N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[F:18][C:19]([Si](C)(C)C)([F:21])[F:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[OH:7][C@@:6]1([C:19]([F:21])([F:20])[F:18])[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:2]1[CH3:1]참가 물질
실험 절차
To a solution (10 mL) of benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (1.0 g) in THF were added trifluoromethyltrimethylsilane (0.95 mL) and 1 mol/L tetrabutylammonium fluoride—THF solution (0.43 mL) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. A 1 mol/L tetrabutylammonium fluoride—THF solution (8.56 mL) was added to the reaction mixture, and the mixture was stirred at 50° C. for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1) to give the title compound as colorless oil (yield: 1.06 g, yield: 81%).
후처리
- temperaturecooling
- stirringthe mixture was stirred at 50° C. for 1 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1)
출처 및 근거
- ORD 기록
- ord-a8b3ab3d72b54ae587b2c20e08dfb699
- 출처 데이터셋
- uspto-grants-2011_09
- 특허 번호
- US08013008B2
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