Reboxetine mesilate, PNU-155950E, FCE-20124, Vestra, Norebox, Edronax

合成路线:Epoxidation of trans-cinnamyl alcohol (A) gives compound (I),which in turn is reacted with sodium 2-ethoxyphenate (B) to give the diol (II).The primary alcoholic group of (II) is reacted with p-nitrobenzoyl chloride to obtain (III),and (IV) is prepared by treatment of (III) with methanesulfonyl chloride.By treatment of (IV) with sodium hydroxide in an aqueous/dioxane solution the epoxide (V) is obtained in high yield,and this reaction causes inversion of configuration at C-2 carbon atom.Treatment of (V) with aqueous methanolic ammonia gives (VI),which in turn is acylated to (VII) with chloroacetyl chloride and cyclized to morpholone (VIII) with potassium tert-butoxide.The reduction to the final compound FCE-20124 is performed with [sodium bis(2-methoxyethoxy)aluminum hydride] (RED-AL) in toluene.

参考文献标题:FCE-20124
文献作者:Riva,F.
参考来源:Drugs Fut 1985,10(11),905


合成路线:Epoxidation of trans-cinnamyl alcohol (A) gives compound (I),which in turn is reacted with sodium 2-ethoxyphenate (B) to give the diol (II).The primary alcoholic group of (II) is reacted with p-nitrobenzoyl chloride to obtain (III),and (IV) is prepared by treatment of (III) with methanesulfonyl chloride.By treatment of (IV) with sodium hydroxide in an aqueous/dioxane solution the epoxide (V) is obtained in high yield,and this reaction causes inversion of configuration at C-2 carbon atom.Treatment of (V) with aqueous methanolic ammonia gives (VI),which in turn is acylated to (VII) with chloroacetyl chloride and cyclized to morpholone (VIII) with potassium tert-butoxide.The reduction to the final compound FCE-20124 is performed with [sodium bis(2-methoxyethoxy)aluminum hydride] (RED-AL) in toluene.
参考文献标题:Configurantional studies on 2[gamma-(2-ethoxyphenoxy)benzyl]morpholine FCE-20124
文献作者:Lazzari,E.; Meroni,M.; Mazzini,G.; Melloni,P.; Della Torre,A.
参考来源:Tetrahedron 1985,41(7),1393