1.1: sodium hydroxide / methanol; water / 12 h / 20 °C 1.2: pH 2 2.1: ammonia; sodium / tetrahydrofuran / 2.5 h / -70 °C / Inert atmosphere 2.2: ice / pH 3 3.1: diphenyl phosphoryl azide; triethylamine / benzene / 6 h / 80 °C 3.2: 30 h / 80 °C 4.1: palladium on carbon; chloroform; hydrogen / methanol / 24 h / 20 °C View Scheme

1.1: bromine; iodine; acetic acid / 1.33 h / 118 °C 2.1: toluene-4-sulfonic acid / 24 h / 64 °C 3.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 72 h / Reflux 4.1: sodium hydroxide / methanol; water / 12 h / 20 °C 4.2: pH 2 5.1: ammonia; sodium / tetrahydrofuran / 2.5 h / -70 °C / Inert atmosphere 5.2: ice / pH 3 6.1: diphenyl phosphoryl azide; triethylamine / benzene / 6 h / 80 °C 6.2: 30 h / 80 °C 7.1: palladium on carbon; chloroform; hydrogen / methanol / 24 h / 20 °C View Scheme

1.1: sodium acetate; acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0 - 10 °C 1.2: 0.5 h / 0 - 20 °C 1.3: 1.33 h / 10 - 50 °C 2.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux View Scheme

1: With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid in tetrahydrofuran T=0 - 10°C; 2: With sodium hydroxide in tetrahydrofuran; water T=0 - 20°C; 0.5 h; 3: With hydrogenchloride in tetrahydrofuran; water T=10 - 50°C; 1.33333 h;