1-Amino-2-propanol → 3-Methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one

HRID 1700426ノート

反応式

HRID 1700426 の反応式
[C:1]1([CH:7]2[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][CH2:16][CH:17](O)[CH3:18]>O1CCCC1>[CH3:18][C:17]1[C:10]2[C:9](=[O:14])[CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][C:11]=2[NH:15][CH:16]=1

参加物

4

反応物 2

HCID 41-Amino-2-propanolHCID 5689621,3-Cyclohexanedione, 5-phenyl-

生成物 1

HCID 183173703-Methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one収率 38.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

A mixture of 5-phenylcyclohexane-1,3-dione (5.0 g), 3-aminopropan-2-ol (2.6 g), molecular sieves 4A (30 g) and tetrahydrofuran (70 ml) was refluxed for 12 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in dimethylformamide (130 ml). To the solution were added 2-bromomesitylene (5.3 g), tetrakistriphenylphosphine palladium (0.77 g) and potassium carbonate (7.3 g), and the mixture was stirred at 150° C. for 4 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane), and the resulting crystals were recrystallized from ethyl acetate-hexane to give colorless crystals of 3-methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (2.3 g).

後処理

  1. temperaturewas refluxed for 12 hours
  2. temperaturecooled
  3. filtrationinsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. dissolutionthe residue was dissolved in dimethylformamide (130 ml)
  6. additionTo the solution were added 2-bromomesitylene (5.3 g), tetrakistriphenylphosphine palladium (0.77 g) and potassium carbonate (7.3 g)
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washthe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified with silica gel column chromatography (EtOAc/hexane)
  13. customthe resulting crystals were recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-1a0fde581eb64ecaa1df7208ff1a76c0
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

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