Reaction of Novel Imide-Reducing Reagents with Pyrrolizidinediones.

The reduction of pyrrolizidinediones with (i-Bu) 2 AlH and LiBHEt 3 affords the corresponding hexahydro-5-hydroxy-3H-pyrrolizin-3-ones in good yield. LiBHEt 3 also reduces N-methylglutarimide. The combination of NaBH 4 /MeOH/Ac 2 O/CH 2 Cl 2 selectivity reduces an imide in the presence of an ester. Hexahydro-5-(methylthio)-3H-pyrrolizin-3-ones are products of the NaBH 4 reduction of pyrolizidinediones in MeSH/CH 2 Cl 2 /Ac 2 O