• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】40410

【品名】6-(2-adamantyl)-2,3,4,5-tetrahydropyridine

【CA登记号】

【 分 子 式 】C15H23N

【 分 子 量 】217.35436

【元素组成】C 82.89% H 10.67% N 6.44%

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:(VIII)

The condensation of adamantan-2-one (I) with 2-pyridyllithium (II) in THF/ethyl ether gives 2-(2-pyridyl)adamantan-2-ol (III), which is treated with dry HCl in ethanol to yield the pyridinium salt (IV). The hydrogenation of (IV) with H2 over PtO2 in ethanol affords 2-(2-piperidinyl)adamantan-2-ol (V), which is treated with SOCl2 in refluxing dichloromethane to provide the piperidinium chloride (VI). The dehydrochlorination of (VI) with KOH in refluxing ethanol yields the tetrahydropyridine (VIII), which is finally hydrogenated with NaBH4 in methanol.

1 Foscolos, G.B.; De Clercq, E.; Kolocouris, A.; Tataridis, D.; Mavromoustalkos, T.; Fytas, G.; Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus a activity relationship study using a combination of NMR spectroscopy and molecular modeling. Bioorg Med Chem Lett 1999, 9, 24, 3465.
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) 40404 2-adamantanone 700-58-3 C10H14O 详情 详情
(II) 34016 2-pyridinyllithium C5H4LiN 详情 详情
(III) 40405 2-(2-pyridinyl)-2-adamantanol C15H19NO 详情 详情
(IV) 40406 2-(2-hydroxy-2-adamantyl)pyridinium chloride C15H20ClNO 详情 详情
(V) 40407 2-(2-piperidinyl)-2-adamantanol C15H25NO 详情 详情
(VI) 40408 2-(2-chloro-2-adamantyl)piperidinium chloride C15H25Cl2N 详情 详情
(VII) 40409 2-tricyclo[3.3.1.1(3,7)]dec-2-ylidenepiperidine C15H23N 详情 详情
(VIII) 40410 6-(2-adamantyl)-2,3,4,5-tetrahydropyridine C15H23N 详情 详情
Extended Information