High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines – A short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines
High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines – A short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines
Scheunemann, M.; Hennig, L.; Funke, U.; Steinbach, J.
Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxy piperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, the highly VAChT affine 4-fluorobenzyltrozamicol was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new β-hydroxy substituted anilidopiperidines.
Keywords: 1-aralkyl-3; 4-epoxy piperidines; 4-fluorobenzyltrozamicol; anilidopiperidines
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Tetrahedron 67(2011), 3448-3456
DOI: 10.1016/j.tet.2011.03.045
Cited 18 times in Scopus
Permalink: https://www.hzdr.de/publications/Publ-15143