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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
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