pyridinium chlorochromate in dichloromethane T=20°C; 1.5 h;

manganese(IV) oxide in dichloromethane T=20°C; 72 h;

in tetrahydrofuran T=-70 - 20°C;

sodium hydrogencarbonate in dimethyl sulfoxide 0.00833333 h; microwave irradiation;

1: With lithium aluminium tetrahydride in tetrahydrofuran T=0 - 25°C; Inert atmosphere; 2: With manganese(IV) oxide in acetonitrile T=20°C; Inert atmosphere;

1: pyrrolidine / dimethylformamide / 110 °C 2: 29 percent / Zn / acetic acid / 2 h / 85 °C View Scheme

1: 29 percent / Zn / acetic acid / 2 h / 85 °C View Scheme

1: 90 percent / p-toluenesulfonic acid monohydrate / toluene / 12 h / Heating 2: 50 percent / tetrahydrofuran / -70 - 20 °C View Scheme

1: 79 percent / pyridinium p-toluene sulfonate / CH2Cl2 / 3 h / 20 °C 2: dimethylformamide / 4 h / 130 °C 3: 48 percent / hydrazine hydrate; Raney nickel / tetrahydrofuran; methanol / 6 h / 20 °C 4: 100 percent / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 60 °C 5: 86 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / 20 °C View Scheme

1: chlorotrimethylsilane; benzyltriethylammonium borohydride / CH2Cl2 / 24 h / 20 °C 2: 79 percent / pyridinium p-toluene sulfonate / CH2Cl2 / 3 h / 20 °C 3: dimethylformamide / 4 h / 130 °C 4: 48 percent / hydrazine hydrate; Raney nickel / tetrahydrofuran; methanol / 6 h / 20 °C 5: 100 percent / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 60 °C 6: 86 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / 20 °C View Scheme