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

HRID 1376055

Reaktionsgleichung

Reaktionsgleichung von HRID 1376055
[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]

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a117f2b43e7b468ab332f7f2092d0dd9
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169777B2

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