반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[H-].[Na+].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20]>CN(C)C=O>[F:20][C:19]([F:22])([F:21])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1참가 물질
반응 조건
- 온도
- 70 °C
실험 절차
A solution of 1.78 g (14 mmol) of 3-quinuclidinol in 20 ml of dry N,N-dimethylformamide (DMF) was added dropwise under nitrogen to a suspension of 0.6 g (15 mmol) of sodium hydride in 20 ml of dry DMF. The mixture was stirred for 15 min at 70° C., and a solution of 3.8 ml (30 mmol) of 2-fluoro-(trifluoromethyl)benzene in 8 ml of dry DMF was added dropwise. The mixture was stirred for another 1.5 h, after which the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with brine. The ethyl acetate layer was separated, dried over magnesium sulfate and evaporated to dryness. The crude compound was purified by column chromatography on silica using methanol-dichloromethane (2:8) as eluent to give 3.0 g (59% yield) of 3-[2-(trifluoromethyl)phenoxy]-1-azabicyclo[2.2.2 ]octane, which was converted into the oxalate salt by treatment with oxalic acid and recrystallization from methanol. m.p. 174° C.
후처리
- stirringThe mixture was stirred for another 1.5 h
- customafter which the solvent was evaporated
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with brine
- customThe ethyl acetate layer was separated
- dry with materialdried over magnesium sulfate
- customevaporated to dryness
- customThe crude compound was purified by column chromatography on silica
출처 및 근거
- ORD 기록
- ord-ec0a81e2fdd044d89fb54e6141d93b73
- 출처 데이터셋
- uspto-grants-1993_11
- 특허 번호
- US05258392
연결된 노트
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