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【结 构 式】 
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【分子编号】29869 【品名】tert-butyl (1R,2R,4S)-2-(6-amino-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate 【CA登记号】 |
【 分 子 式 】C16H23N3O2 【 分 子 量 】289.37764 【元素组成】C 66.41% H 8.01% N 14.52% O 11.06% |
合成路线1
该中间体在本合成路线中的序号：(VI)21) A new synthesis of epibatidine has been reported: The reaction of 2-tosyl-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester (I) with tributyltin hydride (II) by means of azobis(isobutyronitrile) (AIBN) in benzene gives the tin derivative (III), which by treatment with tetrabutylammonium fluoride in THF provides 7-azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester (IV). The condensation of (IV) with 5-iodopyridine-2-amine (V) by means of palladium acetate/tetrabutylammonium chloride/potassium formate in hot DMF yields exo-2-(6-amino-3-pyridyl)-7-azabicyclo[2.2.1]heptane-7-carbo-xylic acid tert-butyl ester (VI), which is finally submitted to diazotization with NaNO2/HCl and treated with CuCl.
| 【1】 Abraham, P.; Brieaddy, L.E.; Carroll, F.I.; Lee, J.R.; Liang, F.; New synthesis of 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-2-ene. A key intermediate in the synthesis of epibatidine and analogs. Tetrahedron Lett 1998, 39, 30, 5321. |
| 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) | 29861 | tert-butyl (1S,4R)-2-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate | C18H23NO4S | 详情 | 详情 | |
| (II) | 29870 | butyl(dipentyl)stannane | C14H32Sn | 详情 | 详情 | |
| (III) | 29866 | tert-butyl (1R,4S)-2-[butyl(dipentyl)stannyl]-3-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]heptane-7-carboxylate | C32H55NO4SSn | 详情 | 详情 | |
| (IV) | 29867 | tert-butyl (1R,4S)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate | C11H17NO2 | 详情 | 详情 | |
| (V) | 29868 | 5-iodo-2-pyridinamine; 5-iodo-2-pyridinylamine | C5H5IN2 | 详情 | 详情 | |
| (VI) | 29869 | tert-butyl (1R,2R,4S)-2-(6-amino-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate | C16H23N3O2 | 详情 | 详情 |