phosphoric acid in ethanol T=-18.8°C; 17 h;

phosphoric acid in ethanol T=50°C; 6 h;

1: With Lindlar's catalyst; hydrogen in ethanol T=20°C; P=760.051 Torr; 16 h; 2: With phosphoric acid in ethanol; ethyl acetate T=50°C; 0.5 h;

in ethanol; water T=50 - 55°C; 1.5 - 2 h;

sodium hydroxide; hydrogen bromide; acetic anhydride; acetic acid; triethylamine; cobalt in ethanol; ethyl acetate; acetone

1: 1.) sodium azide, ammonium chloride, 2.) trimethylphosphine / 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h 2: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 3: 0.98 kg / sodium bicarbonate / hexane / 1 h 4: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme

1: sodium azide / N,N-dimethyl-formamide / 8 h / 90 °C 2: water; triphenylphosphine / tetrahydrofuran / 8 h / Reflux 3: phosphoric acid / ethanol; water; ethyl acetate / 20 - 50 °C View Scheme

1: 0.98 kg / sodium bicarbonate / hexane / 1 h 2: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme

1: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 2: 0.98 kg / sodium bicarbonate / hexane / 1 h 3: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme

1: 95 percent / perchloric acid 2: 1.) BH3-SMe2, trimethylsilyl trifluoromethanesulfonate, 2.) potassium hydroden carbonate / 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h 3: 1.) sodium azide, ammonium chloride, 2.) trimethylphosphine / 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h 4: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 5: 0.98 kg / sodium bicarbonate / hexane / 1 h 6: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme