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【结 构 式】 
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【分子编号】16434 【品名】7-(tert-butyl) 2-methyl (1S,4R)-3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate 【CA登记号】 |
【 分 子 式 】C13H16BrNO4 【 分 子 量 】330.17838 【元素组成】C 47.29% H 4.88% Br 24.2% N 4.24% O 19.38% |
合成路线1
该中间体在本合成路线中的序号：rac-(LXVIII)16) A similar approach was described by Zhang and Trudell in a recent report: The known 7-azabicyclo[2.2.1]heptan-2-one (VIII) was conveniently synthesized by the [4+2] cycloaddition of methyl 3-bromopropynoate (LXVII) and N-BOC-pyrrole (LXVI). They modified Fletcher's synthesis rendering it more stereoselective and suitable for the preparation of (I) on a large scale. The tertiary alcohol (IX) was successfully deoxygenated by a radical reaction via its methyl oxalyl ester with Bu3SnH in the presence of AIBN. This afforded the deoxygenated product stereoselectively as the endo-isomer (Xa).
| 【1】 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210. |
| 【2】 Zhang, C.; Trudell, M.L..; A short and efficient total synthesis of (±)-epibatidine. J Org Chem 1996, 61, 20, 7189-91. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (rac-I) | 16385 | (+)-Epibatidine hydrochloride; (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane | 140111-52-0 | C11H13ClN2 | 详情 | 详情 |
| rac-(LXVIII) | 16434 | 7-(tert-butyl) 2-methyl (1S,4R)-3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate | C13H16BrNO4 | 详情 | 详情 | |
| rac-(VIII) | 16435 | tert-butyl (1R,4S)-2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate | C11H17NO3 | 详情 | 详情 | |
| rac-(IX) | 16436 | tert-butyl (1R,2S,4S)-2-(6-chloro-3-pyridinyl)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate | C16H21ClN2O3 | 详情 | 详情 | |
| rac-(Xa) | 16437 | tert-butyl (1R,2S,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate | C16H21ClN2O2 | 详情 | 详情 | |
| rac-(Xb) | 16438 | tert-butyl (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate | C16H21ClN2O2 | 详情 | 详情 | |
| (LXVI) | 16432 | tert-Butyl pyrrole-1-carboxylate; tert-Butyl-1H-pyrrole-1-carboxylate; tert-Butyl-1-pyrrolecarboxylate | 5176-27-2 | C9H13NO2 | 详情 | 详情 |
| (LXVII) | 16433 | methyl 3-bromo-2-propynoate | C4H3BrO2 | 详情 | 详情 |