ammonia; lithium 2.) hydrolysis; Multistep reaction;

sodium tetrahydroborate in methanol T=0 - 20°C; 1.5 h; Inert atmosphere;

1: With magnesium sulfate; acetic acid in tetrahydrofuran; methanol T=20°C; 0.25 h; 2: With sodium cyanoborohydride in tetrahydrofuran; methanol T=20°C; 12 h;

ammonium acetate; cyano-borane; compound with lithium hydride in ethanol

ammonium acetate; cyano-borane; compound with lithium hydride in ethanol

1: 2.) tetrabutylammonium borohydride, 3.) 2N sulfuric acid / 1.) benzene, reflux, 1 h, 2.) CH2Cl2, -50 deg C to room temperature, 3.) methanol, room temperature, 1 h 2: 1.) 2N NaOH, conc. HCl, 2.) ammonium formiate / 2.) 10percent Pd/C / 1.) methanol, ethyl acetate, 2.) dimethylformamide, reflux, 20 min 3: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature 4: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h View Scheme

ammonium acetate; cyano-borane; compound with lithium hydride in ethanol