Water → (5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

HRID 70543노트

반응식

HRID 70543 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12][O:13][C:14]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:15]=1[CH2:16][N:17]1[C@@H:21]([C:22]#[CH:23])[CH2:20][CH2:19][C:18]1=[O:24].O>C(N(CC)CC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:23]#[C:22][C@@H:21]2[N:17]([CH2:16][C:15]3[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:14]=3[O:13][CH3:12])[C:18](=[O:24])[CH2:19][CH2:20]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 3

HCID 962WaterHCID 1420291-tert-Butyl-4-iodobenzeneHCID 58452699(5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one

생성물 1

HCID 67398609(5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one수율 84%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

Copper iodide (74 mg) and bis(triphenylphosphine)palladium(II) dichloride (135 mg) were added to a solution of 4-tert-butyliodobenzene (3.0 g) in triethylamine (10 mL), and the mixture was stirred at room temperature for 15 minutes. (5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one (1.0 g) was added thereto over one hour, and the mixture was stirred at room temperature for three hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1) to give (5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless powder (1.25 g, 84%).

후처리

  1. waitover one hour
  2. stirringthe mixture was stirred at room temperature for three hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1)

출처 및 근거

ORD 기록
ord-b87af4f26a1349cb8f1f91571641531d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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