1-[2-(Adamantan-1-yl)-2-hydroxyethyl]-1,2,3,6-tetrahydropyridines were obtained by reduction of 1-[(adamantan-1-yl)-2-oxoethyl]-pyridinium bromides. By the action of trifluoromethanesulfonic acid, they undergo carbocationic intramolecular cyclization accompanied by the Wagner–Meerwein rearrangement with the formation of substituted 1-azabicyclo[3.3.1]non-3-enes annulated with the homoadamantane framework. The structure of the obtained compounds was confirmed by spectral methods and X-ray structural analysis.

中文翻译：

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三氟甲磺酸作用下的1- [2-（金刚烷-1-基）-2-羟基乙基] -1,2,3,6-四氢吡啶的转化

通过还原1-[（金刚烷-1-基）-2-氧代乙基]-溴化吡啶得到1- [2-（金刚烷-1-基）-2-羟乙基] -1,2,3,6-四氢吡啶。 。在三氟甲磺酸的作用下，它们经历碳阳离子分子内环化，并伴随Wagner-Meerwein重排，形成被高金刚烷骨架取代的取代的1-azabicyclo [3.3.1] non-3-enes。所得化合物的结构通过光谱法和X射线结构分析确认。