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【结 构 式】 
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【分子编号】16380 【品名】N-[(1R,2R,4S,5S)-4,5-dibromo-2-(6-chloro-3-pyridinyl)cyclohexyl]-2,2,2-trifluoroacetamide 【CA登记号】 |
【 分 子 式 】C13H12Br2ClF3N2O 【 分 子 量 】464.5070696 【元素组成】C 33.61% H 2.6% Br 34.4% Cl 7.63% F 12.27% N 6.03% O 3.44% |
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：rac-(XIII)3) Corey's group published a stereocontrolled route to both enantiomers of epibatidine through HPLC separation of N-(trifluoroacetyl)epibatidine using chiral columns. A Diels-Alder reaction between (Z)-alpha,beta-unsaturated ester (XI) and 1,3-butadiene furnished the cis-4,5-disubstituted cyclohexene (XII), which was converted to the vicinal dibromide (XIII). Upon treatment with t-BuOK, (XIII) underwent intramolecular nucleophilic substitution to give compound (XIV) with the azabicyclo[2.2.1]heptane ring system.
| 【1】 Corey, E.J.; Loh, T.E.; Achyutha-Rao, S.; Daley, D.C.; Sarshar, S.; Stereocontrolled total synthesis of (+)- and (-)-epibatidine. J Org Chem 1993, 58, 5600-2. |
| 【2】 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210. |
| 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-(XII) | 16379 | methyl (1R,6S)-6-(6-chloro-3-pyridinyl)-3-cyclohexene-1-carboxylate | C13H14ClNO2 | 详情 | 详情 | |
| rac-(XIII) | 16380 | N-[(1R,2R,4S,5S)-4,5-dibromo-2-(6-chloro-3-pyridinyl)cyclohexyl]-2,2,2-trifluoroacetamide | C13H12Br2ClF3N2O | 详情 | 详情 | |
| rac-(XIV) | 16381 | 1-[(1R,2S,4R,5R)-2-bromo-5-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]hept-7-yl]-2,2,2-trifluoro-1-ethanone | C12H14BrClN2 | 详情 | 详情 | |
| (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 |
| (XI) | 16378 | methyl (Z)-3-(6-chloro-3-pyridinyl)-2-propenoate | C9H8ClNO2 | 详情 | 详情 |
Extended Information