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

HRID 1670815노트

반응식

HRID 1670815 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-46e41cf7cff54f5c91cbe6e85cd6fc8c
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994176B2

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