hydrogenchloride; ammonia; nickel 1.) EtOH, 75 deg C, 90 min; 100 deg C, 30 min; 2.) EtOH; Yield given. Multistep reaction;

1: 50 percent / Et3N / CHCl3 / 16 h 2: 79 percent / NaNO2 / formic acid / 0.5 h / 0 - 5 °C View Scheme

1: 1) TEA; 2) NaBH4 / 1) room temp., 1 h; 2) room temp. 2h 2: 46.4 percent / hydrogen / 10percent Pd-C / H2O / Ambient temperature 3: 54.5 percent / TEA / acetonitrile / 4 h / Ambient temperature View Scheme

1: 1) TEA; 2) NaBH4 / 1) room temp., 1 h; 2) room temp. 2h 2: 46.4 percent / hydrogen / 10percent Pd-C / H2O / Ambient temperature 3: 54.5 percent / TEA / acetonitrile / 4 h / Ambient temperature 4: 83.1 percent / hydrogen, 1 N aq.HCl / 10percent Pd-C / methanol / 5 h / 40 °C 5: 64.9 percent / TEA / methanol / Ambient temperature 6: 63.4 percent / NaBH4 / methanol / 5 h / Ambient temperature View Scheme

1: 1) TEA; 2) NaBH4 / 1) room temp., 1 h; 2) room temp. 2h 2: 46.4 percent / hydrogen / 10percent Pd-C / H2O / Ambient temperature 3: 54.5 percent / TEA / acetonitrile / 4 h / Ambient temperature 4: 83.1 percent / hydrogen, 1 N aq.HCl / 10percent Pd-C / methanol / 5 h / 40 °C 5: 55.8 percent / TEA / methanol / Ambient temperature 6: 58.9 percent / NaBH4 / methanol / 5 h / Ambient temperature View Scheme

1: 1) TEA; 2) NaBH4 / 1) room temp., 1 h; 2) room temp. 2h 2: 46.4 percent / hydrogen / 10percent Pd-C / H2O / Ambient temperature 3: 54.5 percent / TEA / acetonitrile / 4 h / Ambient temperature 4: 83.1 percent / hydrogen, 1 N aq.HCl / 10percent Pd-C / methanol / 5 h / 40 °C 5: 66.5 percent / TEA / methanol / Ambient temperature 6: 52 percent / NaBH4 / methanol / 5 h / Ambient temperature View Scheme

1: 1) TEA; 2) NaBH4 / 1) room temp., 1 h; 2) room temp. 2h 2: 46.4 percent / hydrogen / 10percent Pd-C / H2O / Ambient temperature 3: 54.5 percent / TEA / acetonitrile / 4 h / Ambient temperature 4: 83.1 percent / hydrogen, 1 N aq.HCl / 10percent Pd-C / methanol / 5 h / 40 °C 5: 48 percent / TEA / methanol / Ambient temperature 6: 56.6 percent / NaBH4 / methanol / 5 h / Ambient temperature View Scheme

Multi-step reaction with 3 steps 1: 2) NaBH4 / 1) methanol, room temp, 1 h; 2) room temp. 2 h2: 77.3 percent / tetrahydrofuran / 0.5 h / Heating3: 84.9 percent / hydrogen, 1N HCl / 10percent Pd-C / H2O; methanol / 40 °C