Asymmetric Synthesis of L-2-Amino[3-11C]butyric Acid, L-[3-11C]Norvaline and L-[3-11C]Valine.

Publisher Website
Google Scholar
Abstract
The short-lived radionuclide 11C (t1/2 = 20.4 min) has been used in the asymmetric synthesis of L-2-amino[3-11C]butyric acid, L-[3-13C]-norvaline and L-[3-13C]valine. The syntheses were performed by alkylation of [(+)-2-hydroxypinanyl-3-idene]glycine tert-butyl ester under anhydrous conditions in tetrahydrofuran/1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone with lithiated 2,2,6,6-tetramethylpiperidine as base, using the appropriate 1C-alkyl iodides prepared in a one-pot reactor from [11C]carbon dioxide. Following removal of the protecting groups, the -[3-11C]amino acids were obtained in 80-82% enantiomeric excess and in 9-25% radiochemical yields, decay corrected and calculated on the basis of the amount of [11C]carbon dioxide at the start of the syntheses within 50-55 min.

This publication has 5 references indexed in Scilit: