(Chemical Equation Presented) A single-step synthesis on a gram scale of four pure stereoisomers of the 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acid was carried out using (R)-1-phenylethylamine to confer chirality. The phenylethyl group, and the p-methoxy group linked to the N-atom, are easily removed by hydrogenolysis to afford the corresponding NH-3 derivatives. A series of N-3-alkyl compounds were prepared by way of a "one-pot" deprotection-alkylation procedure starting from the above key compounds. Their biological activity has been evaluated on the GABA receptor.
An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3-azabicyclo[3.2.1]octane-6-carboxylic acids / M.L. Gelmi, C. Cattaneo, S. Pellegrino, F. Clerici, M. Montali, C. Martini. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 72:25(2007), pp. 9811-9814.
|Titolo:||An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3-azabicyclo[3.2.1]octane-6-carboxylic acids|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2007|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1021/jo7019702|
|Appare nelle tipologie:||01 - Articolo su periodico|