boron tribromide in dichloromethane T=20°C; dealkylation; 9 h;

sodium cyanoborohydride; acetic acid in methanol T=20°C; 2.5 h;

lithium aluminium tetrahydride in 1,4-dioxane Reduction; 0.5 h; Heating;

1: 271 mg / diisopropylethylamine,; benzyltriethylammonium chloride,; palladium(II) acetate / dimethylformamide / 19 h / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 4: 82 percent / benzene; hexane / 0.83 h / Heating 5: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating View Scheme

1: 82 percent / benzene; hexane / 0.83 h / Heating 2: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating View Scheme

1: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 2: 82 percent / benzene; hexane / 0.83 h / Heating 3: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating View Scheme

1: trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 2: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 3: 82 percent / benzene; hexane / 0.83 h / Heating 4: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating View Scheme

1,4-dioxane; lithium aluminium tetrahydride

1: diethyl ether; dimethylamine 2: LiAlH4; dioxane View Scheme