The double Mannich condensation of 2-quinolizidone with formaldehyde and me
thyl amine resulted in the 11-methyl-7,11-diazatricyclo[7.3.1.0(2,7)]tridec
an-13-one of endo-type selectively. The stereochemistry, isomerism and conf
ormational behaviour of derivatives obtained by reduction at C-13 were inve
stigated extensively by one- and two-dimensional H-1, C-13 and N-15 NMR spe
ctroscopy. The site of the protonation and its effect on the conformational
equilibria and chemical shifts were also revealed. (C) 1999 Elsevier Scien
ce B.V. All rights reserved.