formic acid; water

sodium tetrahydroborate in methanol T=25°C; 7 h;

lithium aluminium tetrahydride in tetrahydrofuran 2 h; Heating;

1: With 1,2,3-Benzotriazole in methanol; water T=25°C; Mannich reaction; 4 h; 2: With aluminium trichloride in dichloromethane 10 h; Heating; 3: With sodium tetrahydroborate in tetrahydrofuran T=25°C;

1: AcOH / ethanol / 18 h / Heating 2: NaBH4 / methanol / 1 h / Ambient temperature 3: 78 percent / acetic anhydride / 1 h / 70 °C 4: 86 percent / NaIO4 / H2O; methanol / 16 h / Ambient temperature 5: 1.) TFAA, 2.) BF3*Et2O / 1.) benzene, RT, 1 h, 2.) benzene, RT, 2 h 6: 75 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature 7: 72 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 95 percent / ethanol / 1 h / 60 °C 2: 83 percent / AlCl3 / CHCl3 / 4 h / 25 °C 3: 95 percent / NaBH4 / methanol / 7 h / 25 °C View Scheme

1: 83 percent / AlCl3 / CHCl3 / 4 h / 25 °C 2: 95 percent / NaBH4 / methanol / 7 h / 25 °C View Scheme

1: platinum; acetic acid / Hydrogenation 2: formic acid; water View Scheme

hydrogenchloride; tin

methanol; diethyl ether