1: iron dust, 12 M HCl / methanol / 10 h / Heating 2: Na2CO3 / diethyl ether; H2O / 1.) 0 deg C, 30 min; 2.) room temp., 2 h 3: 77 percent / NaH / dimethylformamide / 3 h / Ambient temperature 4: 89 percent / Jones reagent / acetone / 2 h / Ambient temperature 5: tetrahydrofuran / 2 h / Ambient temperature 6: 5 M aq. NaN3 / H2O / 2 h / Ambient temperature 7: toluene / 1 h / Heating 8: toluene / 2 h / 60 °C 9: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h / Ambient temperature 10: 87 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 11: 80 percent / NaBH3CN / acetic acid / 0.5 h / Ambient temperature 12: 69 percent / NCS / CH2Cl2 / 0.25 h / 0 °C 13: 66 percent / DDQ / CH2Cl2 / 0.08 h 14: 60percent HClO4 / acetic acid / 0.5 h / Ambient temperature 15: 5 M NaOH / methanol / 1 h / Ambient temperature 16: DCC / tetrahydrofuran / 0 °C 17: 80 percent / BH3*SMe2 / tetrahydrofuran / 2 h / Ambient temperature 18: 64 percent / CAN / acetone; H2O / 0.08 h 19: 64 percent / NH4Cl / ethanol / 14 h / Ambient temperature View Scheme

1: H2 / 10percent Pd/C / 3800 Torr 2: pyridine 3: 1.) NaH 4: 100 percent / aq. NaOH 5: pyridine 6: 77 percent / Fremy's salt 7: 41 percent / benzylamine hydrochloride, NaHCO3 / acetonitrile; methanol View Scheme

ammonium cerium(IV) nitrate; ammonium chloride 1) aq. CH3CN, 2) EtOH; Yield given. Multistep reaction;

1: 63 percent / HNO3 / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min 2: 55 percent / NBS / dimethylformamide / 3.08 h / 60 °C 3: 76 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 4: 84 percent / HCl / diethyl ether / 48 h / Heating 5: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 6: 54 percent / Ac2O / 48 h / Ambient temperature 7: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 8: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 9: 100 percent / aq. NaOH / 24 h / Heating 10: ceric ammonium sulfate 11: NH3 View Scheme

1: 55 percent / NBS / dimethylformamide / 3.08 h / 60 °C 2: 76 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 3: 84 percent / HCl / diethyl ether / 48 h / Heating 4: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 5: 54 percent / Ac2O / 48 h / Ambient temperature 6: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 7: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 8: 100 percent / aq. NaOH / 24 h / Heating 9: ceric ammonium sulfate 10: NH3 View Scheme

1: 1.) AcOH, FeCl3, 2.) AcOH / 1.) 60 deg C, 5 min, 2.) reflux, 5 h 2: 63 percent / HNO3 / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min 3: 55 percent / NBS / dimethylformamide / 3.08 h / 60 °C 4: 76 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 5: 84 percent / HCl / diethyl ether / 48 h / Heating 6: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 7: 54 percent / Ac2O / 48 h / Ambient temperature 8: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 9: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 10: 100 percent / aq. NaOH / 24 h / Heating 11: ceric ammonium sulfate 12: NH3 View Scheme

1: 76 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 2: 84 percent / HCl / diethyl ether / 48 h / Heating 3: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 4: 54 percent / Ac2O / 48 h / Ambient temperature 5: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 6: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 7: 100 percent / aq. NaOH / 24 h / Heating 8: ceric ammonium sulfate 9: NH3 View Scheme

1: 84 percent / HCl / diethyl ether / 48 h / Heating 2: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 3: 54 percent / Ac2O / 48 h / Ambient temperature 4: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 5: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 6: 100 percent / aq. NaOH / 24 h / Heating 7: ceric ammonium sulfate 8: NH3 View Scheme

1: 54 percent / Ac2O / 48 h / Ambient temperature 2: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 3: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 4: 100 percent / aq. NaOH / 24 h / Heating 5: ceric ammonium sulfate 6: NH3 View Scheme

1: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 3: 100 percent / aq. NaOH / 24 h / Heating 4: ceric ammonium sulfate 5: NH3 View Scheme