Trimethylaluminum → 2-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide

HRID 1670815ノート

反応式

HRID 1670815 の反応式
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([Cl:13])[C:4]=1[CH2:5][NH2:6].C[Al](C)C.[CH:18]1([CH:24]2[CH2:28][CH2:27][O:26][C:25]2=[O:29])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[CH:18]1([CH:24]([CH2:28][CH2:27][OH:26])[C:25]([NH:6][CH2:5][C:4]2[C:3]([Cl:2])=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=2[Cl:13])=[O:29])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

参加物

5

反応物 3

HCID 16682925TrimethylaluminumHCID 220132343-Cyclohexyl-dihydro-furan-2-oneHCID 673555502,6-Dichloro-4-methoxy-benzylamine hydrochloride

生成物 1

HCID 673553892-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide収率 81%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

Treat a mixture of 2,6-dichloro-4-methoxy-benzylamine hydrochloride (4.0 g, 16.6 mmol) and toluene (100 mL) with trimethylaluminum (2 M in toluene, 16.6 mL, 33.2 mmol) at room temperature for 10 minutes. To the mixture, add a solution of 3-cyclohexyl-dihydro-furan-2-one (2.51 g, 14.94 mmol) in toluene (50 mL). Stir the reaction at reflux for 6 hours. Cool the reaction and quench with HCl (1 N, 50 mL). Partition the mixture with ethyl acetate and HCl (1 N). Separate the organic layer and wash with water and brine. After drying the organic layer over sodium sulfate and filtration, concentrate the filtrate to afford 4.5 g (81%) of the title compound as white solid. MS (m/z): 374 (M+H)+.

後処理

  1. additionTreat
  2. customthe reaction
  3. temperatureat reflux for 6 hours
  4. temperatureCool
  5. customthe reaction
  6. customquench with HCl (1 N, 50 mL)
  7. customPartition the mixture with ethyl acetate and HCl (1 N)
  8. customSeparate the organic layer
  9. washwash with water and brine
  10. customAfter drying the organic layer
  11. filtrationover sodium sulfate and filtration
  12. concentrationconcentrate the filtrate

出典と根拠

ORDレコード
ord-46e41cf7cff54f5c91cbe6e85cd6fc8c
出典データセット
uspto-grants-2011_08
特許番号
US07994176B2

反応ノート

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