Phthalimide → 2-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-1H-isoindole-1,3(2H)-dione

HRID 271824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271824
[CH2:1]([C:8]1[C:9]([CH:18](O)[CH:19]([CH3:21])[CH3:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH2:1]([C:8]1[C:9]([CH:18]([N:27]2[C:23](=[O:33])[C:24]3[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:26]2=[O:28])[CH:19]([CH3:21])[CH3:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 598361951-(3-Benzylquinolin-2-yl)-2-methylpropan-1-ol

Produkt 1

HCID 598361922-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-1H-isoindole-1,3(2H)-dioneAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-ol 13 (102 mg, 1 eq.) in dry tetrahydrofuran (3 ml) at 0° C., was added phthalimide (154 mg, 3 eq), triphenylphosphine (138 mg, 1.5 eq.), and DIAD (1.5 eq., 104 μl). The reaction was allowed to warm to room temperature and stirred overnight. The solvent was evaporated. The residue was dissolved in ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The material was purified by flash chromatography to yield 91 mg of 2-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-1H-isoindole-1,3(2H)-dione 14 as yellow oil.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1afca6560f234cb0a159ec7313394931
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452996B2

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