【药物名称】
化学结构式(Chemical Structure):
参考文献No.726639
标题:Synthesis and biological evaluation of 14-alkoxymorphinans. 18.(1) N-substituted 14-phenylpropyloxymorphinan-6-ones with unanticipated agonist properties: Extending the scope of common structure-activity relationships
作者:Greiner, E.; Spetea, M.; Krassnig, R.; Schullner, F.; Aceto, M.; Harris, L.S.; Traynor, J.R.; Woods, J.H.; Coop, A.; Schmidhammer, H.
来源:J Med Chem 2003,46(9),1758
合成路线图解说明:

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.

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