Ethyl chloroformate → HCID 9906645, compound

Participants

Reaction Steps

In the a) route at scheme 2,2-azabicyclo[2.2.2]octan-3-one(isoquinuclidine-3-one) (4) is treated with sodium hydride (NaH) in DMF, then it is reacted with the intermediate as above (3) in the presence of potassium iodide to yield 2-[3-(4-ethynylphenoxy)propane-1-yl]-2-azabicyclo[2.2.2]octane-3-one (compound 5). Further, compound 5 is treated with n-butyl lithium (n-BuLi), then it is reacted with ethyl chloroformate to obtain ethyl 4-[3-(3-oxo-2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolate (compound 6). Then 4-[3-(3-oxo-2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolic acid (compound 7) is provided by the hydrolysis of compound 6 using 10% sodium hydroxide in water solution (10% NaOHaq).

Provenance & Evidence