hydrogen bromide T=120°C; 18 h; in a sealed tube;

1: 70 percent / ozone / CH2Cl2; methanol / -78 °C 2: 65 percent / CHCl3 / 26 h / 65 °C 3: 1.) 98 percent formic acid, 2.) NaBH3(CN) / 1.) 38 deg C, 1 h, 2.) 20 deg C, 2 h 4: 83 percent / ethanol / 16 h / 78 °C 5: 75 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 6: 83 percent / 48 percent aq. HBr / 18 h / 120 °C View Scheme

1: 75 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 2: 83 percent / 48 percent aq. HBr / 18 h / 120 °C View Scheme

1: 1.) 98 percent formic acid, 2.) NaBH3(CN) / 1.) 38 deg C, 1 h, 2.) 20 deg C, 2 h 2: 83 percent / ethanol / 16 h / 78 °C 3: 75 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 4: 83 percent / 48 percent aq. HBr / 18 h / 120 °C View Scheme

ammonium formate; trifluoroacetic acid; palladium on activated charcoal 1.) methanol, 1 h, reflux; 2.) 17 h, reflux; Yield given. Multistep reaction;

1: 65 percent / CHCl3 / 26 h / 65 °C 2: 1.) 98 percent formic acid, 2.) NaBH3(CN) / 1.) 38 deg C, 1 h, 2.) 20 deg C, 2 h 3: 83 percent / ethanol / 16 h / 78 °C 4: 75 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 5: 83 percent / 48 percent aq. HBr / 18 h / 120 °C View Scheme

1: 65 percent / CHCl3 / 26 h / 65 °C 2: 1.) 98 percent formic acid, 2.) NaBH3(CN) / 1.) 38 deg C, 1 h, 2.) 20 deg C, 2 h 3: 83 percent / ethanol / 16 h / 78 °C 4: 75 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 5: 83 percent / 48 percent aq. HBr / 18 h / 120 °C View Scheme

1: 83 percent / ethanol / 16 h / 78 °C 2: 75 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 83 percent / 48 percent aq. HBr / 18 h / 120 °C View Scheme