4-Iodophenol → 3-(4-Iodophenoxy)-1-azabicyclo[2.2.2]octane

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (37.1 g; 141.5 mmol) solved in dioxane (200 ml) was cooled to 10° C. Diethylazodicarboxylate (24.65 g; 141.5 mmol) was added to the mixture while the temperature was kept below 15° C. (±)3-Quinuclidinol (15.0 g; 117.93 mmol) and 4-iodophenol (28.5 g; 129.7 mmol) was added to the mixture The mixture was stirred at room temperature for 15 hours. Aqueous sodium hydroxide (200 ml; 1 M) was added and the dioxane was evaporated. The mixture was extracted with dichlorometane (2×200 ml), the organic phase was dried and evaporated. Diethylether (150 ml) was added and triphenylphosphine oxide was filtered off. The ether phase was washed with water (100 ml). The organic phase was dried and evaporated followed by column chromatography using a mixture of dichloromethane: methanol (9:1) and aqueous ammonia (1%). The title compound was isolated 8.76 g (23%).

Provenance & Evidence