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 3.1: methyltretrahydrofuran, 2- / 75 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °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 3.1: methyltretrahydrofuran, 2- / 75 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 5.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 6.1: sodium carbonate / o-xylene; water / 70 - 80 °C 6.2: Reflux 6.3: 15 - 55 °C 7.1: ammonia / cyclohexane; water / Reflux 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 3.1: methyltretrahydrofuran, 2- / 75 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 5.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 6.1: sodium carbonate / o-xylene; water / 70 - 80 °C 6.2: Reflux 6.3: 15 - 55 °C View Scheme

chloroform; palladium on carbon; hydrogen in methanol T=20°C; 24 h;

1: 35 g / 1 N NaOH / ethanol; H2O / pH 8.2 2: 1.) B2H6, 2.) concd. HCl / 1.) THF, reflux, 3 h, 2.) reflux, 15 min View Scheme

hydrogenchloride; diborane 1.) THF, reflux, 3 h, 2.) reflux, 15 min; Yield given. Multistep reaction;

1.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 72 h / Reflux 2.1: sodium hydroxide / methanol; water / 12 h / 20 °C 2.2: pH 2 3.1: ammonia; sodium / tetrahydrofuran / 2.5 h / -70 °C / Inert atmosphere 3.2: ice / pH 3 4.1: diphenyl phosphoryl azide; triethylamine / benzene / 6 h / 80 °C 4.2: 30 h / 80 °C 5.1: palladium on carbon; chloroform; hydrogen / methanol / 24 h / 20 °C View Scheme

1.1: toluene-4-sulfonic acid / 24 h / 64 °C 2.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 72 h / Reflux 3.1: sodium hydroxide / methanol; water / 12 h / 20 °C 3.2: pH 2 4.1: ammonia; sodium / tetrahydrofuran / 2.5 h / -70 °C / Inert atmosphere 4.2: ice / pH 3 5.1: diphenyl phosphoryl azide; triethylamine / benzene / 6 h / 80 °C 5.2: 30 h / 80 °C 6.1: palladium on carbon; chloroform; hydrogen / methanol / 24 h / 20 °C View Scheme

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

1.1: diphenyl phosphoryl azide; triethylamine / benzene / 6 h / 80 °C 1.2: 30 h / 80 °C 2.1: palladium on carbon; chloroform; hydrogen / methanol / 24 h / 20 °C View Scheme