Methyl Acrylate → tert-Butyl 1-(2-methoxy-2-oxoethyl)isoindoline-2-carboxylate

HRID 1376055노트

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HRID 1376055 반응식
[CH3:1][O:2][C:3](=[O:21])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(OC)(=O)C=C.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.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:17]([O:16][C:14]([N:13]1[CH2:12][C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]1[CH2:4][C:3]([O:2][CH3:1])=[O:21])=[O:15])([CH3:18])([CH3:20])[CH3:19]

참가 물질

7

반응물 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 692195883-[2-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester

생성물 1

HCID 58777840tert-Butyl 1-(2-methoxy-2-oxoethyl)isoindoline-2-carboxylate수율 71%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

3-[2-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester: To a solution of 161.0 g (561.8 mmol) of material from Part A, 58.0 g (674.2 mmol) of methyl acrylate and 170.5 g (1685.4 mmol) of triethylamine in 800 mL of N,N-dimethylformamide was added 7.9 g (11.2 mmol) of dichlorobis(triphenylphosphine)palladium(II) and the mixture was heated at 80° C. for 32 hr. The mixture was cooled, diluted with 1000 mL of ethyl acetate and washed with 10% aqueous sodium bisulfate. The aqueous portion was extracted three times with ethyl acetate and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in a small amount of dichloromethane and filtered through 7 in. of silica gel in a 2 L sintered glass funnel eluting with 25% ethyl acetate/hexanes. The eluant was concentrated in vacuo and recrystallized from ethyl acetate/hexanes to afford 116.9 g (71%) of the title compound.

후처리

  1. temperatureThe mixture was cooled
  2. washwashed with 10% aqueous sodium bisulfate
  3. extractionThe aqueous portion was extracted three times with ethyl acetate
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in a small amount of dichloromethane
  8. filtrationfiltered through 7 in
  9. washof silica gel in a 2 L sintered glass funnel eluting with 25% ethyl acetate/hexanes
  10. concentrationThe eluant was concentrated in vacuo
  11. customrecrystallized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-a117f2b43e7b468ab332f7f2092d0dd9
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169777B2

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