반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)([O:10][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:9])[CH:5]=[CH:6][CH:7]=1참가 물질
5
반응물 3
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 90 °C
실험 절차
A mixture of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-hydroxyethyl)piperidine-1-carboxylate (0.4395 g, 1.29 mmol), 60% NaH (1.320 g, 33 mmol), and ethyl iodoacetate (5.237 g, 24.5 mmol) in THF (20 mL) was heated at 90° C. for 18 h and then cooled to rt. The reaction mixture was then quenched with saturated brine and extracted with ethyl acetate (3×), dried over Na2SO4. After the solvent was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford 0.0775 g (14%) of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-ethoxy-2-oxoethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 450 (M+Na).
후처리
- temperaturecooled to rt
- customThe reaction mixture was then quenched with saturated brine
- extractionextracted with ethyl acetate (3×)
- dry with materialdried over Na2SO4
- customAfter the solvent was evaporated under reduced pressure
- customthe crude product was purified by reversed-phase HPLC
출처 및 근거
- ORD 기록
- ord-e133ecb36842431cb226d0c1e34b4a8e
- 출처 데이터셋
- uspto-grants-2013_07
- 특허 번호
- US08487108B2
연결된 노트
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