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【结 构 式】 
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【分子编号】38416 【品名】Tropinone; 3-Tropanone; Tropionone; 8-methyl-8-azabicyclo[3.2.1]octan-3-one 【CA登记号】532-24-1 |
【 分 子 式 】C8H13NO 【 分 子 量 】139.19736 【元素组成】C 69.03% H 9.41% N 10.06% O 11.49% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 8-methyl-8-azabicyclo[3.2.1]octan-3-one (I) with hydroxylamine and pyridine in refluxing ethanol gives the oxime (II), which is reduced with LiAlH4 in refluxing 10% H2SO4 yielding endo-methyl-8-azabicyclo[3.2.1]octan-3-amine (III). Finally, this compound is condensed with 1-isopropylbenzimidazole-2-carboxylic acid isopropyl ester (IV) by means of Al(CH3)3 in refluxing toluene. The intermediate 1-isopropylbenzimidazole-2-carboxylic acid isopropyl ester (IV) has been obtained as follows: The cyclization of o-phenylenediamine (V) with 2-hydroxyacetic acid (VI) in refluxing 4N HCl gives 1H-benzyldazole-2-ylmethanol (VII), which is oxidized with KMnO4 to the corresponding carboxylic acid (VIII). Finally, this compound is alkylated and esterified with isopropyl chloride and NaH in DMF.
| 【1】 Labeaga, L.; Alonso-Cires, L.; Tapia, I.; Mosquera, R.; Orjales, A.; Lopez-Tudanca, P.; Benzimidazole-2-carboxylic acid amides and esters: A new structural class of 5-HT3 ligands. Eur J Med Chem 1999, 34, 5, 415. |
| 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) | 38416 | Tropinone; 3-Tropanone; Tropionone; 8-methyl-8-azabicyclo[3.2.1]octan-3-one | 532-24-1 | C8H13NO | 详情 | 详情 |
| (II) | 38412 | 8-methyl-8-azabicyclo[3.2.1]octan-3-one oxime | C8H14N2O | 详情 | 详情 | |
| (III) | 19105 | (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-ylamine; (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine | C8H16N2 | 详情 | 详情 | |
| (IV) | 38413 | isopropyl 1-isopropyl-1H-benzimidazole-2-carboxylate | C14H18N2O2 | 详情 | 详情 | |
| (V) | 12824 | 2-Aminophenylamine; o-Phenylenediamine; 1,2-Benzenediamine | 95-54-5 | C6H8N2 | 详情 | 详情 |
| (VI) | 29856 | 2-hydroxyacetic acid;glycolic acid | 79-14-1 | C2H4O3 | 详情 | 详情 |
| (VII) | 38414 | 1H-benzimidazol-2-ylmethanol | 4856-97-7 | C8H8N2O | 详情 | 详情 |
| (VIII) | 38415 | 1H-benzimidazole-2-carboxylic acid | C8H6N2O2 | 详情 | 详情 |