Ammonium Chloride → (3R*,4S*)-6-methoxy-2,2-dimethyl-7-nitro-4-[(2-phenylethyl)amino]-3,4-dihydro-2H-1-benzopyran-3-ol
Reaktionsgleichung
[O:1]1[C@@H:7]2[C@@H:2]1[C:3]([CH3:18])([CH3:17])[O:4][C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([O:15][CH3:16])=[CH:8][C:6]=12.Cl([O-])(=O)(=O)=O.[Li+].[Cl-].[NH4+:26]>O1CCOCC1>[CH3:16][O:15][C:9]1[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]2[O:4][C:3]([CH3:18])([CH3:17])[C@H:2]([OH:1])[C@@H:7]([NH:26][CH2:2][CH2:7][C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:5]=3)[C:6]=2[CH:8]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of (3R*,4S*)-3,4-epoxy-6-methoxy-2,2-dimethyl-7-nitro-3, 4-dihydro-2H-1-benzopyran (2.50 g, 9.95 mmol) in 1,4-dioxane (5.0 mL), lithium perchlorate (1.06 g, 9.95 mmol) and 4-(phenylethyl)amine (1.50 mL, 11.9 mmol) were added at room temperature and the mixture was stirred at 80° C. for 1 hour. Upon the completion of the reaction, an aqueous solution of saturated ammonium chloride was added to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=6/4) and the aimed product was obtained as orange amorphous substance (quantitative yield).
Aufarbeitung
- customUpon the completion of the reaction
- extractionthe resulting solution was extracted with ethyl acetate
- washThe organic phase was washed with saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationAfter distilling off the solvent
- customthe residue was purified by column chromatography (hexane/ethyl acetate=6/4)
Quellen und Nachweise
- ORD-Eintrag
- ord-0dece4089ceb467397172b244d7af08a
- Quelldatensatz
- uspto-grants-2011_06
- Patentnummer
- US07964623B2
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