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