Methanol → tert-Butyl 5-bromo-1-oxo-1,3-dihydro-2H-isoindole-2-carboxylate
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.[C:12]([O:16][C:17](=O)[O-:18])([CH3:15])([CH3:14])[CH3:13].CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:5]2Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Under nitrogen atmosphere, 1.5 mg of 5-bromo-1-oxo-isoindoline was dissolved in 20 ml of tetrahydrofuran, cooled down to 0° C. Then, 85 mg of N,N-dimethylaminopyridine and 3.0 ml of tert-butylcarbonate were added, and the mixture was stirred at room temperature for 30 min. Methanol was added to the reaction solution, and the solvents were distilled outunder reduced pressure. Water was added to the residues, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=1/2), to obtain 300 mg of the above compound as a white solid.
Aufarbeitung
- distillationthe solvents were distilled outunder reduced pressure
- additionWater was added to the residues
- extractionextracted with ethyl acetate
- washEthyl acetate layer was washed with saturated saline solution
- dry with materialdried with anhydrous sodium sulfate
- distillationAfter distilling out the solvents under reduced pressure
- customthe residues were separated
- custompurified by silicagel column chromatography (ethyl acetate/hexane=1/2)
Quellen und Nachweise
- ORD-Eintrag
- ord-f9f65c4ad27442989954694f20bef825
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07902369B2
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