合成路线1

Alkylation of 14-hydroxycodeinone (I) with cinnamyl bromide (II) in the presence of NaH in DMF gives 14-cinnamyloxycodeinone (III). Catalytic hydrogenation of (III) over Pd/C catalyst affords the corresponding 7,8-dihydro-14-phenylpropoxy derivative (IV). N-Demethylation of (IV) is accomplished by treatment with 1-chloroethyl chloroformate, followed by cleavage of the intermediate chloroethyl carbamate in refluxing MeOH. The resulting N-nor derivative (V) is then alkylated with allyl bromide (VI) using K2CO3 in DMF to provide the N-allyl amine (VII). O-Demethylation of (VII) with boiling 48% HBr yields phenol (VIII). Finally, catalytic hydrogenation of the N-allyl group of (VIII) in the presence of Pd/C affords the title N-propyl derivative.