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【结 构 式】 
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【分子编号】33904 【品名】(2S)-N-benzyl-1-(4-methoxyphenyl)-2-propanamine; N-benzyl-N-[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amine 【CA登记号】 |
【 分 子 式 】C17H21NO 【 分 子 量 】255.35988 【元素组成】C 79.96% H 8.29% N 5.49% O 6.27% |
合成路线1
该中间体在本合成路线中的序号：(III)The bromination of 4 benzyloxy-3-nitroacetophenone (I) with Br2 in CHCl3 gives 4-benzyloxy-3-nitro-alpha-bromoacetophenone (II), which is then condensed with N-benzyl-N-(1-methyl-2-(p-methoxyphenyl)ethyl]-amine (III) in butanone at 80 C yielding 4-benzyloxy-3-nitro-alpha-[N-benzyl-N-[1-methyl-2-(p-methoxyphenyl)ethyl]amino]acetophenone (IV). The reduction of the carbonyl group of (IV) with NaBH4 in ethanol affords the corresponding nitro alcohol (V), which is reduced again with Fe and HCl in ethanol - water to the amino alcohol (VI). The formylation of (VI) with formic acid in acetic anhydride gives 4-benzyloxy-3-formyl-amino-alpha-[N-benzyl-N-[1-methyl-2-(p-methoxyphenyl)ethyl]aminomethyl]benzyl alcohol (VII), which is finally debenzylated with H2 over Pd/C in ethanol and treated with fumaric acid (A).
| 【1】 Murakami, M.; et al.; alpha-Aminomethylbenzylalkoholderivative. DE 2305092; DE 2366625 . |
| 【2】 Castaner, J.; Weetman, D.F.; BD 40A. Drugs Fut 1977, 2, 10, 639. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |
| (I) | 20627 | 1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanone | C15H13NO4 | 详情 | 详情 | |
| (II) | 32763 | 1-[4-(benzyloxy)-3-nitrophenyl]-2-bromo-1-ethanone | C15H12BrNO4 | 详情 | 详情 | |
| (III) | 33904 | (2S)-N-benzyl-1-(4-methoxyphenyl)-2-propanamine; N-benzyl-N-[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amine | C17H21NO | 详情 | 详情 | |
| (IV) | 33900 | 2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanone | C32H32N2O5 | 详情 | 详情 | |
| (V) | 33901 | (1R)-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanol | C32H34N2O5 | 详情 | 详情 | |
| (VI) | 33902 | (1R)-1-[3-amino-4-(benzyloxy)phenyl]-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-ethanol | C32H36N2O3 | 详情 | 详情 | |
| (VII) | 33903 | 5-((1R)-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-hydroxyethyl)-2-(benzyloxy)phenylformamide | C33H36N2O4 | 详情 | 详情 |