[Lactones. 22. Synthesis and reduction of alpha-aminomethylene-delta,delta-diphenyl-delta-valerolactones].

Treatment with tris-(dimethylamino)-methane resp. formylation and reaction with piperidine transfer 1 to 5a,b, which can not be reduced to the corresponding alpha-aminomethyllactones 4a,b, in contrast to the homologue 6 and other alpha-aminomethylene-gamma- and delta-lactones. Isolation of products and gc/ms-investigations verify the reaction course: The aminomethyl moiety in alpha-position of delta,delta-diarylated delta-lactones is instable and eliminates amine to give 7 (NaCNBH3) or 9 (H2/Pt). Only cleavage of the lactone ring enables the formation of stable aminomethyl compounds (10,11). 5a shows weak parasympatholytic and no H1-antihistaminic activity at the isolated guinea-pig ileum.