反応式
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]2参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 45 °C
実験手順
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).
後処理
- 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
出典と根拠
- ORDレコード
- ord-8d145e2c4a544ec4826e0e26586ed956
- 出典データセット
- uspto-grants-2013_08
- 特許番号
- US08507491B2
関連ノート
読み込み中…