반응식
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C1(C)C=CC=CC=1.[N+:26]([C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31]Br)([O-:28])=[O:27]>O1CCCC1>[CH3:1][O:2][C:3](=[O:18])[CH:4]([CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:9][CH2:10]1)[CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=1[N+:26]([O-:28])=[O:27]참가 물질
반응 조건
- 온도
- -78 °C
실험 절차
tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (240 mg, 0.93 mmol) was dissolved in tetrahydrofuran (7 mL). Mixture was cooled to −78° C. A 0.5 M solution of potassium bistrimethylsilyl)amide in toluene (2.2 mL, 1.1 mmol) was added to the mixture drop-wise. Reaction stirred at −78° C. for 20 minutes. A solution of 2-nitrobenzylbromide (240 mg, 1.1 mmol) in tetrahydrofuran (2 mL) was added to the reaction mixture drop-wise. Reaction stirred at −78° C. for 40 minutes. Dry ice bath was removed and the reaction mixture was allowed to warm to room temperature over 30 minutes. Reaction was quenched with aqueous ammonium chloride. Mixture was extracted with ethyl acetate (2×20 mL). Combined extracts were dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as yellow oil in 41% yield. MS m/e (M−C4H8+H)+=337.3.
후처리
- customReaction
- customReaction
- stirringstirred at −78° C. for 40 minutes
- customDry ice bath was removed
- temperatureto warm to room temperature over 30 minutes
- customReaction
- customwas quenched with aqueous ammonium chloride
- extractionMixture was extracted with ethyl acetate (2×20 mL)
- dry with materialCombined extracts were dried (magnesium sulfate)
- filtrationfiltered
- concentrationconcentrated in vacuo
출처 및 근거
- ORD 기록
- ord-fbefab7c72394e35b4538b0b37dec6d6
- 출처 데이터셋
- uspto-grants-2008_06
- 특허 번호
- US07384930B2
연결된 노트
불러오는 중…