An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3- azabicyclo[3.2.1]octane-6-carboxylic acids.
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.
Gelmi
Maria Luisa
ML
Istituto di Chimica Organica A. Marchesini, Facoltà di Farmacia, Università di Milano, Via Venezian 21, I-20133 Milano, Italy. marialuisa.gelmi@unimi.it
Cattaneo
Cristian
C
Pellegrino
Sara
S
Clerici
Francesca
F
Montali
Marina
M
Martini
Claudia
C
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
D002264:Carboxylic Acids; D014326:Tropanes