hydrogen; platinum(IV) oxide in ethanol T=20°C; Reduction; 2 h;

ammonium hydroxide T=20°C; 120 h;

1.1: NaBH4 / methanol 1.2: 70 percent / PBr3 / Heating 2.1: 82 percent / NaN3 / dimethylformamide / 17 h / 20 °C 3.1: 94 percent / H2 / PtO2 / aq. ethanol / 2 h / 20 °C View Scheme

1: 82 percent / MgSO4 / diethyl ether / 10 h / 20 °C 2: 84 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 3: 85 percent / Bu3SnH; AIBN / benzene / 4 h / Heating 4: NaBH4 / ethanol / 0.5 h / 20 °C 5: 415.1 mg / EDC / CH2Cl2 / 16 h / 20 °C 6: 98 percent / MCPBA / CH2Cl2 / 0.5 h / 0 °C 7: 63 percent / CaCO3 / toluene / 13 h / Heating 8: methanol / 1.5 h / 20 °C / Irradiation 9: 2.8 mg / Pd/C / acetic acid / 3 h / 80 °C View Scheme