Tetrahydrofuran → (+/-)-(3aR*,7aS*)-7a-(2,2-difluorobenzo[1,3]dioxol-4-yl)hexahydropyrano[3,4-c]isoxazole
Reaktionsgleichung
C1COCC1.Br[C:7]1[C:15]2[O:14][C:13]([F:17])([F:16])[O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[N:18]1[O:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][C:22]=12.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.C1COCC1>[F:16][C:13]1([F:17])[O:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C@:22]34[CH2:23][O:24][CH2:25][CH2:26][C@H:21]3[CH2:20][O:19][NH:18]4)[C:15]=2[O:14]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
THF (2.0 ml) was added to a solution of 4-bromo-2,2-difluoro-1,3-benzodioxol (1.96 g) in toluene (20 ml). The mixture was cooled to −78° C., and a solution of (±)-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole obtained in Preparation Example 1-(2) (500 mg) in toluene-THF (10:1) (10 ml) and a boron trifluoride-diethyl ether complex (990 μl) were added dropwise at the same time. After stirring at the same temperature for two hours, an ammonium chloride solution was added to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (873 mg).
Aufarbeitung
- additiona boron trifluoride-diethyl ether complex (990 μl) were added dropwise at the same time
- customto terminate
- customthe reaction
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-31e5add7439042dbb9cab2f889fb90f9
- Quelldatensatz
- uspto-grants-2012_06
- Patentnummer
- US08198269B2
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