Toluene → (S)-tert-butyl 1-oxohexan-2-ylcarbamate
Reaktionsgleichung
CO[C:3](=[O:17])[C@H:4]([CH2:13][CH:14]([CH3:16])C)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:18]1(C)C=CC=CC=1>>[C:9]([O:8][C:6]([NH:5][C@@H:4]([CH2:13][CH2:14][CH2:16][CH3:18])[CH:3]=[O:17])=[O:7])([CH3:10])([CH3:11])[CH3:12]Komponenten
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
Under an argon gas stream, N-(tert-butoxycarbonyl)-(L)-leucine methyl ester (9.8 g, 40 mmol) as dissolved in toluene (70 ml), and cooled to -78° C. To the solution, while keeping the temperature at -60 to -70° C., was added gradually aluminum diisobutyl hydride (toluene 1.0 M solution, 52 ml). After stirring at -78° C. for 40 minutes, the cooling bath was removed, and methanol (2.1 ml) and 20% aqueous citric acid solution (30 ml) were added to the mixture, followed by extraction with ethyl acetate. The organic layer was washed with 20% aqueous citric acid solution, a saturated aqueous sodium bicarbonate solution, water and a saturated aqueous sodium chloride solution, successively. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give (S)-2-(tert-butoxycarbonylamino)-5-methylpentanal (8.5 g).
Aufarbeitung
- customat -60 to -70° C.
- customthe cooling bath was removed
- additionmethanol (2.1 ml) and 20% aqueous citric acid solution (30 ml) were added to the mixture
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with 20% aqueous citric acid solution
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-5cbecad3b4d24217babc559ec29aa4b8
- Quelldatensatz
- uspto-grants-2000_05
- Patentnummer
- US06066672
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