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

反応式

[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

参加物

反応物 4

HCID 702Ethanol

HCID 712Formaldehyde

HCID 1118Sulfuric Acid

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

生成物 1

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

実験手順

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.