1: With lithium aluminium tetrahydride in diethyl ether T=20°C; 3 h; 2: With water; potassium hydroxide in diethyl ether

hydrogen; palladium on activated charcoal in methanol P=2250.18 Torr;

tetrahydrofuran; lithium aluminium tetrahydride

trifluoroacetic acid in dichloromethane T=20°C; 20 h; Inert atmosphere;

1: 99 percent / aq. Na2CO3 / CH2Cl2 2: 82 percent / LiBH4 / tetrahydrofuran / 0.5 h / 20 °C 3: 87 percent / H2; aq. HCl / Pd/C / methanol / 2 h View Scheme

1: 82 percent / LiBH4 / tetrahydrofuran / 0.5 h / 20 °C 2: 87 percent / H2; aq. HCl / Pd/C / methanol / 2 h View Scheme

sodium tetrahydroborate; amberlyst-15; lithium chloride 1.) CH3OH; 2.) THF, reflux, 3-4 h; Yield given. Multistep reaction;

1.1: 70 percent / NaOH / dioxane / 3 h / 20 °C 2.1: NaH / dimethylformamide / 0.17 h / 0 °C 2.2: 74 percent / dimethylformamide / 5 h / 20 °C 3.1: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 4.1: 1.95 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 5.1: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 6.1: 2.6 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 7.1: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 8.1: 411 mg / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C 9.1: 96 percent / H2 / 10 percent Pd/C / dimethylformamide / 18 h / 20 °C 10.1: 6N HCl / 18 h / 105 °C View Scheme

1: 1.95 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 2: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 3: 2.6 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 4: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 5: 411 mg / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C 6: 96 percent / H2 / 10 percent Pd/C / dimethylformamide / 18 h / 20 °C 7: 6N HCl / 18 h / 105 °C View Scheme

1: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 2: 1.95 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 3: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 4: 2.6 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 5: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 6: 411 mg / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C 7: 96 percent / H2 / 10 percent Pd/C / dimethylformamide / 18 h / 20 °C 8: 6N HCl / 18 h / 105 °C View Scheme