Reaktionsgleichung
[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[C:4](=O)[CH2:3][CH2:2]2.C1(C)C=CC(S([CH2:20][N+:21]#[C-])(=O)=O)=CC=1.C(O)C.CC(C)([O-])C.[K+]>C(COC)OC>[N:1]12[CH2:9][C@H:5]([CH2:6][CH2:7][CH2:8]1)[C@H:4]([C:20]#[N:21])[CH2:3][CH2:2]2Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 5 °C
Versuchsvorschrift
To a solution of 2.00 g of 1-azabicyclo[3.3.1]nonan-4-one in 100 ml of dimethoxyethane, 3.65 g of p-toluenesulfonylmethylisocyanide and 1.13 g of ethanol were added, followed by cooling to 5° C. Then, 4.00 g of potassium tert-butoxide was added while keeping the internal temperature below 10° C. The mixture was stirred at room temperature for 30 minutes, followed by further stirring at 40° C. for 30 minutes. The precipitate thus formed was removed by filtration. The residue obtained by evaporation of the solvent was purified by an alumina column chromatography (eluent: chloroform:hexane=1:1). The resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1), whereby 1.01 g of (4R*,5R*)-1-azabicyclo[3.3.1]nonane-4-carbonitrile was obtained.
Aufarbeitung
- customthe internal temperature below 10° C
- stirringby further stirring at 40° C. for 30 minutes
- customThe precipitate thus formed
- customwas removed by filtration
- customThe residue obtained by evaporation of the solvent
- customwas purified by an alumina column chromatography (eluent: chloroform:hexane=1:1)
- customThe resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-2e57fe313bf04f39bdf3ad8a3c083277
- Quelldatensatz
- uspto-grants-1998_11
- Patentnummer
- US05834499
Verknüpfte Notizen
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