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【结 构 式】 
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【分子编号】29863 【品名】tert-butyl (1R,2R,3S,4S)-2-(6-methoxy-3-pyridinyl)-3-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]heptane-7-carboxylate 【CA登记号】 |
【 分 子 式 】C24H30N2O5S 【 分 子 量 】458.57868 【元素组成】C 62.86% H 6.59% N 6.11% O 17.44% S 6.99% |
合成路线1
该中间体在本合成路线中的序号：(V)20) A total synthesis of epibatidine has been reported: The cyclization of 1-(tert-butoxycarbonyl)pyrrole (I) with tosylacetylene (II) by means of H2 over Pd/C in acetonitrile gives the bicyclic compound (III), which is condensed with 5-bromo-2-methoxypyridine (IV) by means of BuLi in THF yielding the 2exo-(6-methoxy-3-pyridyl) derivative (V). The detosylation of (V) by means of Na(Hg) in methanol/THF affords intermediate (VI), which is treated with POCl3 in DMF to effect the conversion of the methoxypyridine into the desired chloropyridine derivative (VII), with simultaneous elimination of the tert-butoxycarbonyl protecting group and N-formylation. Finally, this formyl group is eliminated with HCl in hot THF.
| 【1】 Giblin, G.M.P.; Jones, C.D.; Simpkins, N.S.; The total synthesis of the analgesic alkaloid epibatidine. J Chem Soc - Perkins Trans I 1998, 22, 3689. |
| 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) | 16432 | tert-Butyl pyrrole-1-carboxylate; tert-Butyl-1H-pyrrole-1-carboxylate; tert-Butyl-1-pyrrolecarboxylate | 5176-27-2 | C9H13NO2 | 详情 | 详情 |
| (II) | 29860 | ethynyl 4-methylphenyl sulfone; ethynyl(4-methylphenyl)dioxo-lambda(6)-sulfane | 13894-21-8 | C9H8O2S | 详情 | 详情 |
| (III) | 29861 | tert-butyl (1S,4R)-2-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate | C18H23NO4S | 详情 | 详情 | |
| (IV) | 29862 | 5-bromo-2-methoxypyridine; 5-bromo-2-pyridinyl methyl ether | 13472-85-0 | C6H6BrNO | 详情 | 详情 |
| (V) | 29863 | tert-butyl (1R,2R,3S,4S)-2-(6-methoxy-3-pyridinyl)-3-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]heptane-7-carboxylate | C24H30N2O5S | 详情 | 详情 | |
| (VI) | 29864 | tert-butyl (1R,2R,4S)-2-(6-methoxy-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate | C17H24N2O3 | 详情 | 详情 | |
| (VII) | 29865 | (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carbaldehyde | C12H13ClN2O | 详情 | 详情 |