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【结 构 式】

【分子编号】36426

【品名】1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol

【CA登记号】

【 分 子 式 】C27H33NO3

【 分 子 量 】419.56396

【元素组成】C 77.29% H 7.93% N 3.34% O 11.44%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

The bromination of 4-benzyloxyacetophenone (VI) with Br2 in dioxane gives 4-benzyloxyphenacyl bromide (VII), which by reduction with NaBH4 in dioxane and epoxidation with NaOH water is converted into (I). The condensation of 4-benzyloxystyrene oxide (I) with 1,1-dimethyl-3-(2-methoxyphenyl)propylamine (II) in refluxing isopropanol gives 1-(4-benzyloxyphenyl)-2-[1,1-dimethyl-3-(2-methoxyphenyl)propylamino]ethanol (III), which is debenzylated by reduction with H2 over Pd/C in ethanol, and treated with HCl.

1 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 .
2 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 36425 2-[4-(benzyloxy)phenyl]oxirane; benzyl 4-(2-oxiranyl)phenyl ether C15H14O2 详情 详情
(II) 36422 3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine C12H19NO 详情 详情
(III) 36426 1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol C27H33NO3 详情 详情
(VI) 36423 1-[4-(benzyloxy)phenyl]-1-ethanone 54696-05-8 C15H14O2 详情 详情
(VII) 36424 1-[4-(benzyloxy)phenyl]-2-bromo-1-ethanone C15H13BrO2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

The oxidation of (VI) with SeO2 in hot dioxane-water gives 4-benzyloxyphenylglyoxal (IV). The condensation with (II) in refluxing ethanol, gives 4-benzyloxy-alpha-[1,1-dimethyl-3-(2-methoxyphenyl)propylimino]acetophenone (V), which is then reduced with NaBH4 in ethanol to afford (III), which is debenzylated by reduction with H2 over Pd/C in ethanol, and treated with HCl.

1 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 .
2 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 36422 3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine C12H19NO 详情 详情
(III) 36426 1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol C27H33NO3 详情 详情
(IV) 31696 2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde C15H12O3 详情 详情
(V) 36427 1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]imino]-1-ethanone C27H29NO3 详情 详情
(VI) 36423 1-[4-(benzyloxy)phenyl]-1-ethanone 54696-05-8 C15H14O2 详情 详情
Extended Information