A novel reductive ring-opening reaction of isoxazolidine to form functionalized 1,3-amino-alcohol

Reductive cleavage of the NO bond of isoxazolidine ring with catalytic hydrogenation over Raney nickel was described. Bicyclic isoxazolidines could be effectively converted into the corresponding 1,3-amino-alcohol possessing a sultone or sultam moiety with high conversion and yield when the hydrogenation was catalyzed by freshly prepared Raney nickel under a pressure of 40 psi in the presence of triethylamine.