SYNTHESIS OF DESMETHYL TIAGABINE

The title compound has been investigated as one in a series of novel a nd selective GABA uptake inhibitors that exhibit potent anti-convulsan t effects. Versatile syntheses have been developed for the preparation of this compound in excellent yields. Key steps are a Grignard reacti on followed by ring opening with simultaneous dehydration and brominat ion of a hydroxymethyl cyclopropane with bromotrimethylsilane; displac ement of bromine with ethyl R-(-)-piperidine-3-carboxylate and an acid or base catalyzed hydrolysis of the ester moiety.