trifluoroacetic acid in dichloromethane T=20°C; 6 h;

1: 40 percent / hydrogen / platinum(IV)oxide / ethanol / 0.5 h / Ambient temperature 2: Li in liq. NH3 View Scheme

lithium in ammonium hydroxide

1: 97 percent / 4-(dimethylamino)pyridine / toluene / 40 h / Heating 2: 76 percent / diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / 1.) toluene, -78 deg C, 30min, 2.) -60 deg C, 1.5 h 3: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature 4: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C 5: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 6: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 7: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

1: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C 2: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 3: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 4: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

1: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 2: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

1: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 2: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 3: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

1: 76 percent / diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / 1.) toluene, -78 deg C, 30min, 2.) -60 deg C, 1.5 h 2: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature 3: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C 4: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 5: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 6: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

1: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature 2: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C 3: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 4: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 5: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

1: 1.) lithium diisopropyl amide / 1.) THF, -78 deg C, 5 min 2: 97 percent / 4-(dimethylamino)pyridine / toluene / 40 h / Heating 3: 76 percent / diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / 1.) toluene, -78 deg C, 30min, 2.) -60 deg C, 1.5 h 4: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature 5: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C 6: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 7: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 8: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme