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【结 构 式】

【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%

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:(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
Extended Information