Ethanol → 1-Azatricyclo(3.3.1.1,3,7)decan-4-one

Reaktionsgleichung

[CH2:1]=O.OS(O)(=O)=O.[NH2:8][CH2:9][CH:10]1[CH2:19]C[C:13]2(OCCO2)[CH2:12][CH2:11]1.[CH3:20][CH2:21][OH:22]>>[N:8]12[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:19][CH:20]([C:21]3=[O:22])[CH2:1]1)[CH2:9]2

Komponenten

Edukt 4

HCID 702Ethanol

HCID 712Formaldehyde

HCID 1118Sulfuric Acid

HCID 109539781-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamine

Produkt 1

HCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-oneAusbeute 69 %

Versuchsvorschrift

Paraformaldehyde (2.2 g), in 320 ml 2% v/v H2SO4, is heated to boiling and 2.7 g (0.016 mole) of 8-aminomethyl-1,4-dioxaspiro[4,5]decane in 20 ml EtOH, is added over 4 hours. This mixture is then heated at reflux for 24 hours. The cooled reaction is washed with dichloromethane, then basified with 10N NaOH and extracted with dichloromethane. The combined extracts are dried over MgSO4 and stripped to dryness, giving 1.68 g (69%) of product.