Codorphone hydrochloride, Conorphone hydrochloride, Conorfone hydrochloride, TR-5109

考诺封 Chemical Name: 17-Cyclopropylmethyl-4,5alpha-epoxy-8beta-ethyl-3-methoxymorphinan-6-one hydrochloride
CAS No. 70865-14-4, 72060-05-0 (free base)
项目整合开发状态: Phase II
项目研究机构: Pars (Originator)
合成路线:This compound can be obtained in two related ways:1) The reaction of codeinon (I) with ethyllithium and CuI in ether gives 4,5alpha-epoxy-8beta-ethyl-3-methoxy-17-methylmorphinan-6-one (II),which by treatment with cyanogen bromide and K2CO3 in CHCl3 is converted into 17-cyano-4,5alpha-epoxy-8beta-ethyl-3-methoxymorphinan-6-one (III).Elimination of the cyano group of (III) by treatment with refluxing aqueous 2N HCl yields 4,5alpha-epoxy-8beta-ethyl-3-methoxymorphinan-6-one (IV),which is finally alkylated with cyclopropylmethyl bromide (C) and NaHCO3 in DMF at 100 C.2) The reaction of codeinon (I) with vinyl bromide (A),tert-butyllithium and CuI in ether gives 4,5alpha-epoxy-3-methoxy-17-methyl-8beta-vinylmorphinanone (V),which is reduced with H2,Pd/C in ethanol to yield (II).