sodium dithionite; ammonia in methanol; water T=20°C; 12 h;

1: NaH / dimethylformamide / Ambient temperature 2: NaH / dimethylformamide 3: H2 / PtO2 / ethyl acetate / Ambient temperature View Scheme

1: NaH / dimethylformamide 2: H2 / PtO2 / ethyl acetate / Ambient temperature View Scheme

1: NaH / dimethylformamide / Ambient temperature 2: NaH / dimethylformamide 3: H2 / PtO2 / ethyl acetate / Ambient temperature View Scheme

1.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / water; acetonitrile; tert-butyl alcohol / 0.17 h / 20 °C / Inert atmosphere 2.1: diphenyl phosphoryl azide; triethylamine / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / Reflux; Inert atmosphere 3.1: potassium hydroxide / ethanol / 18 h / Reflux; Inert atmosphere View Scheme

potassium hydroxide in ethanol 18 h; RefluxInert atmosphere;

1.1: diphenyl phosphoryl azide; triethylamine / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 1.2: 2 h / Reflux; Inert atmosphere 2.1: potassium hydroxide / ethanol / 18 h / Reflux; Inert atmosphere View Scheme

1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / Inert atmosphere 2.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / water; acetonitrile; tert-butyl alcohol / 0.17 h / 20 °C / Inert atmosphere 3.1: diphenyl phosphoryl azide; triethylamine / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 3.2: 2 h / Reflux; Inert atmosphere 4.1: potassium hydroxide / ethanol / 18 h / Reflux; Inert atmosphere View Scheme

1: K2CO3; acetone 2: acetic acid; aqueous HNO3 3: sodium dithionite; aqueous ethanol View Scheme

1: acetic acid; aqueous HNO3 2: sodium dithionite; aqueous ethanol View Scheme