1.1: acetic acid / methanol / 1 h / 20 °C 1.2: 25 - 45 °C 2.1: sodium hydroxide; water / methanol / 6 h / 20 °C View Scheme

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;

1.1: acetic acid / methanol / 1 h / 20 °C 1.2: 25 - 45 °C 2.1: sodium hydroxide; water / methanol / 6 h / 20 °C 3.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 6 h / 20 °C View Scheme

Multi-step reaction with 3 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 115 - 120 °C2.2: 20 °C / pH 3 - 4 / Acidic conditions3.1: sulfuric acid / 1,4-dioxane; water / 5 h / 95 - 100 °C