SYNTHESIS OF (S)-3,4-DIAMINOBUTANENITRILES AS PRECURSORS FOR 3-AMINO-GABA DERIVATIVES

Starting from natural asparagine (1) a synthesis of the protected (S)-3,4-diaminobutanenitriles 5 and 8a-c via the beta-homoserine derivative 2 is described. The amino function in position 4 was introduced by Mitsunobu-coupling or by reductive amination when a strange deformylation of the amino aldehyde 7 was observed as a side reaction. The Mitsunobu-product 5 was converted into the dibenzylamine substituted GABA 6b which was investigated for its affinity at the GABA-A receptor.