Tetrahedron

High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3, 4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel …

M Scheunemann, L Hennig, U Funke, J Steinbach

Index: Scheunemann, Matthias; Hennig, Lothar; Funke, Uta; Steinbach, Joerg Tetrahedron, 2011 , vol. 67, # 19 p. 3448 - 3456

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Citation Number: 9

Abstract

Abstract Nucleophilic ring-opening reactions of three 1-aralkyl-3, 4-epoxypiperidines 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, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of ...