triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran T=50°C;

1: 71 percent / dimethylformamide dineopentyl acetal / acetonitrile / 2 h / 80 °C 2: 33 percent / sodium dithionite / tetrahydrofuran; H2O View Scheme

sodium tetrahydroborate in methanol 2 h;

Fremy’s salt; sodium dihydrogen phosphate buffer in acetone 1 h; Ambient temperature;

1: 1.) KH / 1.) DMF, RT, 45 min, 2.) DMF, RT, 1h 2: 83 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 3: 1.) NaH 4: 81 percent / Bu3SnH, AIBN / benzene / 5 h / Heating 5: 1.) POCl3 / 1.) -5 deg C, 30 min, 2.) 35 deg C, 1 h 6: 81 percent / H2 / 10percent Pd/C / tetrahydrofuran / 12 h / 2327.2 Torr 7: 85 percent / potassium nitrodisulfonate / H2O; acetone / 2 h 8: 89 percent / NaBH4 / methanol / 2 h View Scheme

1: 81 percent / Bu3SnH, AIBN / benzene / 5 h / Heating 2: 1.) POCl3 / 1.) -5 deg C, 30 min, 2.) 35 deg C, 1 h 3: 81 percent / H2 / 10percent Pd/C / tetrahydrofuran / 12 h / 2327.2 Torr 4: 85 percent / potassium nitrodisulfonate / H2O; acetone / 2 h 5: 89 percent / NaBH4 / methanol / 2 h View Scheme

1: aq. sodium dithionite / ethanol; CHCl3 2: 1.) DIBAL, 2.) FeCl3, aq. HCl / 1.) CH2Cl2, -30 deg C, 2 h, 2.) CH2Cl2, -30 deg C View Scheme

tin(ll) chloride in methanol T=20°C; 0.166667 h;

1: tin; hydrogenchloride / ethanol / |Reflux 2: Fremy’s salt / acetone; aq. phosphate buffer / pH 6.4 3: sodium tetrahydroborate / methanol View Scheme

1: Fremy’s salt / acetone; aq. phosphate buffer / pH 6.4 2: sodium tetrahydroborate / methanol View Scheme