ammonia; sodium in 1,4-dioxane T=-78°C; Birch Reduction; 2 h;

ammonia; sodium in toluene 1) -60 deg C, 3 h, 2) room temperature, 20 h;

1: 0.285 g / diethyl ether; methanol 2: Na, liquid ammonia / toluene / 1) -60 deg C, 3 h, 2) room temperature, 20 h View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 0 °C 2.1: 5 palladium on charcoal; hydrogen / methanol / 24 h / 20 °C 3.1: sodium hydroxide / methanol; water / 17 h / 0 °C 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 5.1: trichlorophosphate / toluene / 16 h / |Reflux 5.2: 6 h / -78 °C 6.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 7.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme

1.1: |Electrochemical reaction 2.1: |Electrochemical reaction 3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 0 °C 4.1: 5 palladium on charcoal; hydrogen / methanol / 24 h / 20 °C 5.1: sodium hydroxide / methanol; water / 17 h / 0 °C 6.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 7.1: trichlorophosphate / toluene / 16 h / |Reflux 7.2: 6 h / -78 °C 8.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 9.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme

1.1: tetrabutyl-ammonium chloride; hydrogenchloride / water; acetonitrile / |Electrochemical reaction 2.1: |Electrochemical reaction 3.1: |Electrochemical reaction 4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 0 °C 5.1: 5 palladium on charcoal; hydrogen / methanol / 24 h / 20 °C 6.1: sodium hydroxide / methanol; water / 17 h / 0 °C 7.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 8.1: trichlorophosphate / toluene / 16 h / |Reflux 8.2: 6 h / -78 °C 9.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 10.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme

1.1: |Electrochemical reaction 2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 0 °C 3.1: 5 palladium on charcoal; hydrogen / methanol / 24 h / 20 °C 4.1: sodium hydroxide / methanol; water / 17 h / 0 °C 5.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 6.1: trichlorophosphate / toluene / 16 h / |Reflux 6.2: 6 h / -78 °C 7.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 8.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme

1.1: methanol / 20 °C 2.1: sodium hydroxide / methanol; water / 17 h / 0 °C 3.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 4.1: trichlorophosphate / toluene / 16 h / |Reflux 4.2: 6 h / -78 °C 5.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 6.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme

1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 2.1: trichlorophosphate / toluene / 16 h / |Reflux 2.2: 6 h / -78 °C 3.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 4.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme

1.1: trichlorophosphate / toluene / 16 h / |Reflux 1.2: 6 h / -78 °C 2.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 3.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme