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【结 构 式】 
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【分子编号】32839 【品名】1'-Ethyl-3,5,6,7-tetrahydro-2H-spiro[furo[2,3-f]indole-3,4'-piperidine]; 5-Acetyl-1'-ethyl-3,5,6,7-tetrahydro-2H-spiro[furo[2,3-f]indole-3,4'-piperidine] 【CA登记号】 |
【 分 子 式 】C18H24N2O2 【 分 子 量 】300.40084 【元素组成】C 71.97% H 8.05% N 9.33% O 10.65% |
合成路线1
该中间体在本合成路线中的序号：(VI)Quaternization of 4-pyridylcarbinol (I) by means of iodoethane provided pyridinium salt (II), which was reduced with NaBH4 to the tetrahydropyridine (III). Subsequent Mitsunobu coupling of (III) with 1-acetyl-6-bromo-2,3-dihydro-1H-indol-5-ol (IV) afforded ether (V). Intramolecular cyclization of (V) to the spiro compound (VI) was effected by treatment with tributyltin hydride and azobis(isobutyronitrile). The acetamide function of (VI) was then hydrolyzed by refluxing with HCl in H2O-EtOH to furnish intermediate diamine (VII).
| 【1】 Gaster, L.M.; King, F.D.; Wyman, P.A. (GlaxoSmithKline plc); Tetracyclic spiro cpds., process for their preparation and their use as 5HT1D receptor antagonists. EP 0799226; JP 1998510821; US 5972951; WO 9619477 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10925 | Iodoethane;ethyl iod | 75-03-6 | C2H5I | 详情 | 详情 | |
| (I) | 32835 | 4-pyridinylmethanol | 586-95-8 | C6H7NO | 详情 | 详情 |
| (II) | 32836 | 1-ethyl-4-(hydroxymethyl)pyridinium iodide | C8H12INO | 详情 | 详情 | |
| (III) | 32837 | (1-ethyl-1,2,3,6-tetrahydro-4-pyridinyl)methanol | C8H15NO | 详情 | 详情 | |
| (IV) | 19324 | 1-(6-bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)-1-ethanone | C10H10BrNO2 | 详情 | 详情 | |
| (V) | 32838 | 1-[6-bromo-5-[(1-ethyl-1,2,3,6-tetrahydro-4-pyridinyl)methoxy]-2,3-dihydro-1H-indol-1-yl]-1-ethanone | C18H23BrN2O2 | 详情 | 详情 | |
| (VI) | 32839 | 1'-Ethyl-3,5,6,7-tetrahydro-2H-spiro[furo[2,3-f]indole-3,4'-piperidine]; 5-Acetyl-1'-ethyl-3,5,6,7-tetrahydro-2H-spiro[furo[2,3-f]indole-3,4'-piperidine] | C18H24N2O2 | 详情 | 详情 | |
| (VII) | 32844 | 1'-Ethyl-3,5,6,7-tetrahydro-2H-spiro[furo[2,3-f]indole-3,4'-piperidine] | C16H22N2O | 详情 | 详情 |