2-(2-hydroxy-2-adamantyl)pyridinium chloride -Drug Synthesis Database

【结构式】

【分子编号】40406

【品名】2-(2-hydroxy-2-adamantyl)pyridinium chloride

【CA登记号】

【分子式】C₁₅H₂₀ClNO

【分子量】265.78264

【元素组成】C 67.79% H 7.58% Cl 13.34% N 5.27% O 6.02%

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：(IV)

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.

参考文献中间体

合成目标

【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