Trifluoroacetic acid → 2-(3-Methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester
반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:9]([CH3:24])([CH3:23])[CH:8]2O)=[O:4].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:9]([CH3:24])([CH3:23])[CH2:8]2)=[O:4]참가 물질
반응 조건
- 온도
- 25 °C
실험 절차
To a stirred mixture solution of 4-hydroxy-2-(3-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (3.4 g, 10.2 mmol) and triethylsilane (6.0 mL) at 25° C. was added trifluoroacetic acid (3.0 mL) dropwise. The resulting mixture solution was stirred at 25° C. for 3 hours. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with saturated aqueous sodium bicarbonate solution (4×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was triturated with methanol. The resulting precipitate was collected, dried in vacuo to afford 2-(3-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.6 g, 50%) as a white solid: LC/MS m/e calcd for C20H23NO3 (M+H)+: 326.41, observed: 326.2.
후처리
- concentrationThen the reaction mixture was concentrated in vacuo
- extractionthe residue was extracted with ethyl acetate (2×200 mL)
- washwashed with saturated aqueous sodium bicarbonate solution (4×100 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was triturated with methanol
- customThe resulting precipitate was collected
- customdried in vacuo
출처 및 근거
- ORD 기록
- ord-0b7eccb6ed034f249200ae35973eba11
- 출처 데이터셋
- uspto-grants-2013_11
- 특허 번호
- US08586747B2
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