3,6-Dichloropyridazine → (Rac.)-4-(6-chloro-pyridazin-3-yloxy)-1-aza-bicyclo[3.3.1]nonane

Participants

Reaction Conditions

Reaction Steps

Potassium trimethylsilylamine (5.25 mmol) is added to a solution of (rac.)-1-Aza-bicyclo[3.3.1]nonan-4-ol (5.0 mmol) in THF (20 ml) at room temperature and the solution is stirred for 30 min. The resulting potassium alcoholate is slowly added to a precooled solution of 3,6-dichloropyridazine (7.5 mmol) in THF (50 ml) and the resulting mixture is stirred for another 20 minutes. The solution is allowed to warm to 0° C. is quenched with brine and extracted with diethylether. The organic layer is dried over magnesium sulfate and evaporated. The brown oil is purified by silica gel column chromatography (CH2Cl2:MeOH:NH3, 9:1:0.1) to afford (rac.)-4-(6-Chloro-pyridazin-3-yloxy)-1-aza-bicyclo[3.3.1]nonane (320 mg).

Provenance & Evidence