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

Temperature

10 °C

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%).

1. customwas kept below 15° C.
2. additionwas added to the mixture The mixture
3. customthe dioxane was evaporated
4. extractionThe mixture was extracted with dichlorometane (2×200 ml)
5. customthe organic phase was dried
6. customevaporated
7. additionDiethylether (150 ml) was added
8. filtrationtriphenylphosphine oxide was filtered off
9. washThe ether phase was washed with water (100 ml)
10. customThe organic phase was dried
11. customevaporated
12. additiona mixture of dichloromethane: methanol (9:1) and aqueous ammonia (1%)

ORD record

ord-9c1119f9c3d744e592bdd7e3004c50bc

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652010B2