1: 95 percent / hydrogen, triethylamine / platinum oxide / ethyl acetate / 3 h / 25 °C 2: 88 percent / 1.) triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) 0 deg C, 30 min then 25 deg C, 1 h View Scheme

hydrogen; triethylamine; platinum(IV) oxide in ethyl acetate T=25°C; 3 h;

1: 95 percent / hydrogen, triethylamine / platinum oxide / ethyl acetate / 3 h / 25 °C 2: 88 percent / 1.) triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) 0 deg C, 30 min then 25 deg C, 1 h 3: 65 percent / 2N aq. sodium hydroxide / 3 h / 100 °C View Scheme

hydrazine hydrate in ethanol 3 h; Heating;