sodium hypophosphite; nickel in pyridine; water; acetic acid T=80°C; Reduction; 63 h;

1: With methanesulfonic acid; trifluorormethanesulfonic acid T=100°C; 2 h; 2: With water T=0 - 5°C; 0.5 h; Product distribution / selectivity;

1: 63 percent / iron; acetic acid / methanol; H2O / 1 h / 40 °C 2: 93 percent / triethylamine / CH2Cl2 / 19 h / 20 °C 3: 80 percent / triphenylphosphine (polymer-bound); carbon tetrachloride / 24 h / Heating 4: 4.42 g / sodium azide / acetic acid / 4 h / 70 °C 5: 90 percent / tetrakis(triphenylphosphine)palladium(0) / dimethylformamide / 20 h / 80 °C 6: 80 percent / Raney nickel; sodium hypophosphite / pyridine; acetic acid; H2O / 63 h / 80 °C View Scheme

1: 80 percent / triphenylphosphine (polymer-bound); carbon tetrachloride / 24 h / Heating 2: 4.42 g / sodium azide / acetic acid / 4 h / 70 °C 3: 90 percent / tetrakis(triphenylphosphine)palladium(0) / dimethylformamide / 20 h / 80 °C 4: 80 percent / Raney nickel; sodium hypophosphite / pyridine; acetic acid; H2O / 63 h / 80 °C View Scheme

1: 90 percent / tetrakis(triphenylphosphine)palladium(0) / dimethylformamide / 20 h / 80 °C 2: 80 percent / Raney nickel; sodium hypophosphite / pyridine; acetic acid; H2O / 63 h / 80 °C View Scheme

Multistep reaction;