反応式
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH3:27])[CH2:9][C:10]1[C:18]2[C:13](=[C:14]([O:19][CH2:20][C:21]3C=CC=CC=3)[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].BrCC#[N:32].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH3:27])[CH2:9][C:10]1[C:18]2[C:13](=[C:14]([O:19][CH2:20][C:21]#[N:32])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 80 °C
実験手順
The crude {1-methyl-2-[7-hydroxy-1H-indol-3-yl]ethyl}-carbamic acid tert-butyl ester from above (29.2 g, 102 mmol theory) is dissolved in methyl ethyl ketone (300 mL) and bromoacetonitrile (20.4 mL, 306 mmol) and potassium carbonate (33.8 g, 250 mmol) is added. The mixture is heated at 80° C. for 2 hours. The solids are removed by filtration, the cake is washed with methyl ethyl ketone, and the combined filtrates are concentrated by rotary evaporation. The crude product is purified by flash chromatography (500 g silica gel, eluted with 8×500 mL dichloromethane, 4×500 mL 5% ethyl acetate/dichloromethane, 6×500 mL 10% ethyl acetate/dichloromethane). The fractions containing product are concentrated and hexane is added to the solution to precipitate out the product affording 23.7 g (70.2% yield) of racemic {1-methyl-2-[7-cyanomethoxy-1H-indol-3-yl]ethyl}-carbamic acid tert-butyl ester.
後処理
- customThe solids are removed by filtration
- washthe cake is washed with methyl ethyl ketone
- concentrationthe combined filtrates are concentrated by rotary evaporation
- customThe crude product is purified by flash chromatography (500 g silica gel, eluted with 8×500 mL dichloromethane, 4×500 mL 5% ethyl acetate/dichloromethane, 6×500 mL 10% ethyl acetate/dichloromethane)
- additionThe fractions containing product
- concentrationare concentrated
- additionhexane is added to the solution
- customto precipitate out the product
出典と根拠
- ORDレコード
- ord-2f4f310b00424901a50b0647432141ec
- 出典データセット
- uspto-grants-2005_06
- 特許番号
- US06911463B2
関連ノート
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