Nowatorska i wydajna synteza SV119

N-(9-(6-Aminohexyl)-9-azabicycIo[3.3.1]nonan-3-yl)-N-(2-methoxy-5-methylphenyl)carbamate hydrochloride (SV119) was synthesized by subsequent reaction of CO(CH2 COOH)(2), pentanedial and PhNH2 center dot HCl in aq. soln. in presence of AcONa at 0 degrees C, isolation of raw 9-benzyl-9-azabicyc-IO(3.3.1]nonan-3-one, its conversion with Al(O-i-Pr)(3) to 9-benzyl-9-azabicycIo[3.3.1]nonan-3-ol at 110 degrees C for 6 h, and then to 9-benzyl-9-azabicycIo[3.3.1]nonan-3-yl-2-methoxy-5-methylphenylcarbamate by reaction with 2-methoxy-5-methylphenylisocyanate and SnBu2(OAc)(2) at room temp. The carbamate was converted to 9-azabicycIo[3.3.1]nonan-3-yl-2-methoxy-5-methylphenylcarbamate by reacting with ammonium formate on Pd(OH)(2)/C under boiling in MeOH/EtOAc soln. and finally to the title compd. by conversion with an N-(6-bromoallcyl)phthalimide and with NH2NH2 under reflux in EtOH for 2 h. The total yield of the synthetic was 62%. The structure of all intermediates and final product was confirmed with H-1-NMR and IR spectra and by elementary anal.