반응식
Cl.[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.CCN([CH:19]([CH3:21])[CH3:20])C(C)C.[BH-](OC(C)=O)(OC(C)=O)[O:23]C(C)=O.[Na+].[CH2:36]1C[O:39][CH2:38][CH2:37]1>C(OCC)(=O)C>[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:36][C@H:37]1[CH2:38][O:39][C:19]([CH3:20])([CH3:21])[O:23]1)[CH2:8]2참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 45 °C
실험 절차
A mixture containing 5-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (249 mg, 1 mmol), (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxyaldehyde (260 mg, 2 mmol), DIEA (0.2 ml, 1 mmol) and Na(OAc)3BH (440 mg, 2 mmol) in THF (1 ml) is heated at 45° C. for 18 hours. After cooling to room temperature, the reaction mixture is diluted with ethyl acetate. The organic layer is washed with saturated aqueous NaHCO3 solution, water, brine, dried over MgSO4 and concentrated to dryness by rotary evaporation. The crude product is purified by silica gel flash chromatography, eluted with 30% ethyl acetate in dichloromethane to yield (S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1,2,3,4-tetrahydroisoquinoline as a brown oil. LC-MS m/z: 326.1 (M+1).
후처리
- temperatureAfter cooling to room temperature
- washThe organic layer is washed with saturated aqueous NaHCO3 solution, water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated to dryness by rotary evaporation
- customThe crude product is purified by silica gel flash chromatography
- washeluted with 30% ethyl acetate in dichloromethane
출처 및 근거
- ORD 기록
- ord-8d145e2c4a544ec4826e0e26586ed956
- 출처 데이터셋
- uspto-grants-2013_08
- 특허 번호
- US08507491B2
연결된 노트
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