hydrogenchloride; palladium 10 on activated carbon; hydrogen in methanol; water T=20°C; P=11251.1 Torr; 3 h;

1: With sodium hydroxide in methanol T=20°C; 0.5 h; Inert atmosphere; 2: With dihydrogen peroxide in methanol T=20°C; 8 h; Inert atmosphere; Solvent;

dihydrogen peroxide; sodium hydroxide in dimethyl sulfoxide T=0 - 20°C; 3.41667 h; Inert atmosphere;

1: 1-(3-benzoyloxypropyl)-7-cyano-5-(2R-aminopropyl)-2,3-dihydroindole With dihydrogen peroxide; sodium hydroxide in dimethyl sulfoxide 2 h; 2: [2-(2,2,2-trifluoroethoxy)phenoxy]acetaldehyde With acetic acid in methanol T=25 - 30°C; 1 h; 3: With sodium cyanoborohydride in methanol T=40 - 45°C; 2 h;

sodium tetrahydroborate; ethanol in tetrahydrofuran T=50 - 55°C; 6 h;

trimethylsilyl iodide in dichloromethane T=20°C; 0.5 h; Inert atmosphere;

methanesulfonic acid; palladium 10 on activated carbon; hydrogen in ethanol; water T=30 - 35°C; 3 h; AutoclaveInert atmosphere;

in ethyl acetate T=15 - 55°C;

1.1: N,N-dimethyl-formamide / 150 °C / Inert atmosphere 1.2: 0.25 h / 70 °C 2.1: ammonium acetate / 4.5 h / 125 °C 2.2: 0.5 h / 20 °C 3.1: hydrogenchloride; water; iron; anhydrous iron chloride / 2.5 h / 60 - 90 °C 4.1: tetrahydrofuran / 0.17 h / 20 °C 4.2: 24 h / 20 °C 5.1: sodium carbonate / water / 0.5 h / 20 °C 6.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 21.5 h / 110 °C / Sealed tube 7.1: hydrogen / 5 palladium on charcoal / ethanol / 19 h / 50 °C / 9000.9 Torr 8.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 3.42 h / 0 - 20 °C / Inert atmosphere View Scheme

1.1: bromine; acetic acid / 0.67 h / 20 °C 2.1: N,N-dimethyl-formamide / 150 °C / Inert atmosphere 2.2: 0.25 h / 70 °C 3.1: ammonium acetate / 4.5 h / 125 °C 3.2: 0.5 h / 20 °C 4.1: hydrogenchloride; water; iron; anhydrous iron chloride / 2.5 h / 60 - 90 °C 5.1: tetrahydrofuran / 0.17 h / 20 °C 5.2: 24 h / 20 °C 6.1: sodium carbonate / water / 0.5 h / 20 °C 7.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 21.5 h / 110 °C / Sealed tube 8.1: hydrogen / 5 palladium on charcoal / ethanol / 19 h / 50 °C / 9000.9 Torr 9.1: sodium hydroxide; dihydrogen peroxide / water; dimethyl sulfoxide / 20.17 h / 20 °C / Cooling with ice; Inert atmosphere 10.1: trimethylsilyl iodide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere View Scheme