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Potassium Carbonate → racemic {1-methyl-2-[7-cyanomethoxy-1H-indol-3-yl]ethyl}-carbamic acid tert-butyl ester

HRID 8098
ノート
印刷プレビュー

反応式

HRID 8098 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 11485811{1-Methyl-2-[7-(benzyloxy)-1h-indol-3-yl]ethyl}-carbamic acid tert-butyl ester

生成物 1

HCID 69518565racemic {1-methyl-2-[7-cyanomethoxy-1H-indol-3-yl]ethyl}-carbamic acid tert-butyl ester収率 70.2%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

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

  1. customThe solids are removed by filtration
  2. washthe cake is washed with methyl ethyl ketone
  3. concentrationthe combined filtrates are concentrated by rotary evaporation
  4. 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)
  5. additionThe fractions containing product
  6. concentrationare concentrated
  7. additionhexane is added to the solution
  8. customto precipitate out the product

出典と根拠

ORDレコード
ord-579ccc08061142699e0875fb06cf892e
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07087635B2

反応ノート

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