pyridinium chlorochromate 2 h; Ambient temperature;

1: 85 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 2: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 3: 87 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 2: 87 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: 81 percent / acetonitrile / 120 h / Heating 2: 85 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 3: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 4: 87 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: 50 percent / SOCl2 / 2 h / Heating 3: 89 percent / KOH, NH2NH2*H2O / various solvent(s) / 6 h / 200 °C 4: 22 percent View Scheme

1: 94 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 12 h / -78 - 20 °C 2: COCl2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C View Scheme

1: 94 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 12 h / -78 - 20 °C 2: COCl2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C View Scheme

1: 38 percent / conc. hydrochloric acid / 12 h / 170 °C 2: 81 percent / diborane / tetrahydrofuran / 3 h / -10 °C 3: 92.3 percent / diethyl ether / 2 h / Heating 4: p-toluenesulfonic acid / benzene / 16.5 h / Heating 5: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 6: 60 percent / phosphorus tribromide / diethyl ether / 3 h / Heating 7: 1.) lithium, ammonia, 2.) dimethylsulfoxide / 2.) THF, a) 2 h, b) 4 h 8: 100 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 9: 76 percent / H2 / Pd/C / ethanol 10: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 60 percent / phosphorus tribromide / diethyl ether / 3 h / Heating 2: 1.) lithium, ammonia, 2.) dimethylsulfoxide / 2.) THF, a) 2 h, b) 4 h 3: 100 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 4: 76 percent / H2 / Pd/C / ethanol 5: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 92.3 percent / diethyl ether / 2 h / Heating 2: p-toluenesulfonic acid / benzene / 16.5 h / Heating 3: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 4: 60 percent / phosphorus tribromide / diethyl ether / 3 h / Heating 5: 1.) lithium, ammonia, 2.) dimethylsulfoxide / 2.) THF, a) 2 h, b) 4 h 6: 100 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 7: 76 percent / H2 / Pd/C / ethanol 8: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme