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

Full Text: HTML

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 ...

Related Articles:

Development of two diastereoselective routes towards trans-4-aminomethyl-piperidin-3-ol building blocks

[Gijsen, Harrie J.M.; De Cleyn, Michel J.A.; Love, Christopher J.; Surkyn, Michel; Van Brandt, Sven F.A.; Verdonck, Marc G.C.; Moens, Luc; Cuypers, Jef; Bosmans, Jean-Paul R.M.A. Tetrahedron, 2008 , vol. 64, # 10 p. 2456 - 2464]

Fliposomes: new amphiphiles based on trans-3, 4-bis (acyloxy)-piperidine able to perform a pH-triggered conformational flip and cause an instant cargo release from …

[Samoshin, Andrey V.; Veselov, Ivan S.; Chertkov, Vyacheslav A.; Yaroslavov, Alexander A.; Grishina, Galina V.; Samoshina, Nataliya M.; Samoshin, Vyacheslav V. Tetrahedron Letters, 2013 , vol. 54, # 41 p. 5600 - 5604]

More Articles...