1.1: zinc; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 70 °C / |Inert atmosphere; |Large scale 1.2: 1 h / 20 °C / |Large scale 2.1: sulfuryl dichloride / tert-butyl methyl ether / 1.5 h / 20 - 23 °C / |Large scale 3.1: triethylamine / N,N-dimethyl-formamide / 14 h / 55 °C / |Inert atmosphere; |Large scale 4.1: ammonium acetate / propan-1-ol; ethanol / 1 h / 50 °C / |Inert atmosphere; |Large scale 5.1: sodium cyanoborohydride; alpha-hydroxyethanoic acid / methanol / 20 °C / |Inert atmosphere; |Large scale 6.1: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale View Scheme

1.1: zinc; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 70 °C / |Inert atmosphere; |Large scale 1.2: 1 h / 20 °C / |Large scale 2.1: sulfuryl dichloride / tert-butyl methyl ether / 1.5 h / 20 - 23 °C / |Large scale 3.1: triethylamine / N,N-dimethyl-formamide / 14 h / 55 °C / |Inert atmosphere; |Large scale 4.1: ammonium acetate / propan-1-ol; ethanol / 1 h / 50 °C / |Inert atmosphere; |Large scale 5.1: sodium cyanoborohydride; alpha-hydroxyethanoic acid / methanol / 20 °C / |Inert atmosphere; |Large scale 6.1: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale 7.1: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / |Large scale 8.1: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C 9.1: acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaMnO4 / tert-butyl methyl ether; water / 12 °C View Scheme

potassium hydroxide in ethanol

(i) Et2O, (ii) aq. HCl; Multistep reaction;

in dimethyl sulfoxide T=60 - 70°C; 3 h;

potassium cyanide in ethanol; water

in ethanol; water Heating / reflux;

in dimethyl sulfoxide T=85°C; 4.66667 h; Inert atmosphereLarge scale;

in dimethyl sulfoxide T=130°C; 1.5 h;

sodium iodide in dimethyl sulfoxide T=20°C; 72 h;