Triethyl orthoacetate → (+/-) 3-(5-Methyl-1,3,4-oxadiazol-2-yl)-1-azabicyclo [2.2.2]octane
Reaktionsgleichung
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([NH:11][NH2:12])=[O:10])[CH2:2]2.[C:13](OCC)(OCC)(OCC)[CH3:14]>>[CH3:13][C:14]1[O:10][C:9]([CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)=[N:11][N:12]=1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
(±) 1-Azabicyclo[2.2.2]octane-3-carboxylic acid hydrazide (D8) (0.36 g; 2.1 mmoles) and triethyl orthoacetate (3 ml) were heated at 120° C. for 2 h. Excess triethyl orthoacetate was evaporated in vacuo and the residue was heated for a further 2 h at 140° C. The reaction was diluted with water (10 ml), saturated with potassium carbonate and extracted into ether (3×15 ml). Combined organic extracts were dried (Na2SO4) and concentrated to give the title compound as an oil (0.29 g; 72%), which was purified as the oxalate salt. m.p. 147°-8° (Acetone-methanol).