Synthesis of the 3-hydroxy oxiracetam enantiomers, potential nootropic drugs

Article abstract of DOI:10.1016/S0957-4166(00)82227-2

The enantioselective synthesis of the potentially nootropic compounds 3-6 is reported. Derivative 3 was obtained from the readily available L-tartaric acid, by reduction of the imide 8 prepared with methyl glycinate. The other derivatives 4-6 were obtained from the dihydroxylactam 11. Protection of one of the hydroxyl groups and a Mitsunobu reaction or triflate displacement of the other group produces the remaining stereoisomers. Aminoderivatives 25 and 27 were obtained by displacement with sodium azide and reduction.