Triethylamine → 2-[3-(2,2-Dimethyl[1,3]dioxolan-4-yl)propyl]isoindole-1,3-dione

HRID 1245774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245774
[CH3:1][C:2]1([CH3:11])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][NH2:10])[CH2:4][O:3]1.[C:12]([C:17]1[CH:27]=[CH:26][CH:25]=[C:19]2C(N[C:23](=[O:24])[C:18]=12)=O)(OCC)=[O:13].C(N(CC)CC)C>C(#N)C>[CH3:1][C:2]1([CH3:11])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][N:10]2[C:12](=[O:13])[C:17]3[C:18](=[CH:19][CH:25]=[CH:26][CH:27]=3)[C:23]2=[O:24])[CH2:4][O:3]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 134166863-(2,2-Dimethyl-1,3-dioxolan-4-yl)propan-1-amineHCID 22254400Ethoxycarbonylphthalimide

Produkt 1

HCID 219154692-[3-(2,2-Dimethyl[1,3]dioxolan-4-yl)propyl]isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(2,2-dimethyl-[1,3]dioxolan-4-yl)propylamine (1.05 g, 6.60 mmol) and carboethoxyphthalimide (1.45 g, 6.60 mmol) in acetonitrile (10 mL) at room temperature was added triethylamine (0.92 mL, 6.60 mmol) in one portion and the resuting mixture was stirred at room temperature for 18 hours, evaporated in vacuo and the residue was dissolved in ethyl acetate (50 mL). The solution was washed with brine, 10% citric acid solution and brine, then dried over anhydrous magnesium sulfate. Filtration and concentration in vacuo gave an oil which was purified by column chromatography on silica using ethyl acetate-petroleum ether mixture as eluent to afford a colourless oil.

Aufarbeitung

  1. customevaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washThe solution was washed with brine, 10% citric acid solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration and concentration in vacuo
  6. customgave an oil which
  7. customwas purified by column chromatography on silica
  8. customto afford a colourless oil

Quellen und Nachweise

ORD-Eintrag
ord-095a2f07d6ed468486a571819a8ffc8f
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125904B2

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