Synthesis of substituted 1-[2-(adamantan-1-yl)ethyl]piperidines

V. A. Shadrikova; E. V. Golovin; E. A. Kuznetsova; M. Yu. Rostova; Yu. N. Klimochkin

doi:10.1134/S1070428016100146

Synthesis of substituted 1-[2-(adamantan-1-yl)ethyl]piperidines

Authors: Shadrikova V.A.¹, Golovin E.V.¹, Kuznetsova E.A.¹, Rostova M.Y.¹, Klimochkin Y.N.¹
Affiliations:
1. Samara State Technical University
Issue: Vol 52, No 10 (2016)
Pages: 1452-1462
Section: Article
URL: https://journal-vniispk.ru/1070-4280/article/view/215064
DOI: https://doi.org/10.1134/S1070428016100146
ID: 215064

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Abstract

Quaternary 1-[2-(adamantan-1-yl)ethyl]pyridinium bromides were reduced with sodium tetrahydridoborate in ethanol, and hydroarylation of the resulting 1-[2-(adamantan-1-yl)ethyl]-1,2,3,6-tetrahydropyridines with benzene in trifluoromethanesulfonic acid afforded phenylpiperidines with preferentially equatorial orientation of the phenyl substituent.