新产品编号:2462101

Chemical Name: 4,5alpha-Epoxy-3-hydroxy-14beta-(3-phenylpropoxy)-17-propylmorphinan-6-one hydrochloride
项目整合开发状态: Preclinical
项目研究机构: Universit鋞 Innsbruck (Originator), University of Maryland (Originator), University of Michigan (Originator), Virginia Commonwealth University (Originator)
合成路线: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.