Study of a reduction step during the continuous synthesis of N-amino-3-azabicyclo[3.3.0]octane. Kinetics, modelling, and optimization

The reduction of N-chloro-3-azabicyclo[3.3.0]octane with sodium borohydride at different pH values and variable concentrations of the haloamine and reducing agent was studied. The reaction was found to be second order and exhibited a specific acid catalysis. The enthalpy and entropy of activation were determined at pH 12.89. A mathematical treatment of the kinetic data allowed a complete characterization of the final state and the determination of percentage of haloamine reduced as a function of temperature, [NaBH4]/[haloamine] ratio, arid pH. A reaction mechanism is proposed.