in tetrahydrofuran 24 h;

hydrogenchloride in 1,4-dioxane 2 h; Ambient temperature;

hydrogen; palladium on activated charcoal in methanol

1: 76 percent / NaHCO3, m-chloroperbenzoic acid / CH2Cl2 / 3 h / 5 °C 2: 91 percent / LiN3, NH4Cl / dimethylformamide; H2O / 32 h / 70 °C 3: 70 percent / ammonium formate / 10percent Pd/C / methanol / 2.5 h / Ambient temperature 4: 89 percent / HCl / dioxane / 2 h / Ambient temperature View Scheme

1.1: diethyl ether; toluene / 1 h / -78 °C 1.2: 684 mg / NaBH4 / methanol; diethyl ether; toluene / 72 h / -78 - 20 °C 2.1: 80 percent / HCOONH4 / 10percent Pd/C / propan-2-ol / 0.33 h / microwave irradiation View Scheme

1: 78 percent / MgSO4 / CH2Cl2 / 0.5 h 2: diethyl ether / 3 h / -55 °C 3: 89 percent / H2 / Pd(OH)2 / acetic acid; ethanol / 15 h / 760 Torr 4: 92 percent / 4.8 M HCl/dioxane / 20 h / Ambient temperature View Scheme

1: 80 percent / MgSO4 / CH2Cl2 / 0.5 h 2: 1.) Et2AlCl / diethyl ether / 1.( r.t., 30 min; 2.) -78 deg C, 3 h 3: 89 percent / H2 / Pd(OH)2 / acetic acid; ethanol / 15 h / 760 Torr 4: 92 percent / 4.8 M HCl/dioxane / 20 h / Ambient temperature View Scheme

1: 70 percent / H2, ammonium formate / 10percent Pd/C 2: HCl, dioxane View Scheme