5-Trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester → 5-Ethyl-6-trifluoromethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 1930871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930871
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH:21]=[CH2:22])=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]2[C:15](=[CH:14][C:13]([C:17]([F:20])([F:18])[F:19])=[C:12]([CH2:21][CH3:22])[CH:11]=2)[CH2:16]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 1

HCID 577533965-Trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 577535725-Ethyl-6-trifluoromethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl esterAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution 0.54 mmol 5-trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester in 50 ml methanol was added 50 mg 10% palladium on charcoal and the mixture was stirred under an atmosphere of hydrogen (0.6 bar positive pressure) for 72 h. The reaction mixture was then filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (20% yield). MS (m/e): 260.0 ([M+H-Me2C═CH2]+, 100%).

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6c97ac5a9d8c4cc59816f3d751c37d52
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188139B2

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