hydrogen; palladium on activated charcoal

1: With methanol T=20°C; 3 h; 2: With sodium carbonate T=20°C; 48 h;

1: 90 percent / NaN3, NaH / dimethylformamide / 6 h / 23 °C 2: H2 / 10percent Pd/C / ethanol / 12 h / 23 °C / 760 Torr View Scheme

1: oxalyl chloride / toluene / 1.5 h 2: liq. NH3 3: triethylamine / pentane / 0.5 h / 23 °C 4: I2 / tetrahydrofuran / 0.17 h 5: 90 percent / NaN3, NaH / dimethylformamide / 6 h / 23 °C 6: H2 / 10percent Pd/C / ethanol / 12 h / 23 °C / 760 Torr View Scheme

1: triethylamine / pentane / 0.5 h / 23 °C 2: I2 / tetrahydrofuran / 0.17 h 3: 90 percent / NaN3, NaH / dimethylformamide / 6 h / 23 °C 4: H2 / 10percent Pd/C / ethanol / 12 h / 23 °C / 760 Torr View Scheme

1: liq. NH3 2: triethylamine / pentane / 0.5 h / 23 °C 3: I2 / tetrahydrofuran / 0.17 h 4: 90 percent / NaN3, NaH / dimethylformamide / 6 h / 23 °C 5: H2 / 10percent Pd/C / ethanol / 12 h / 23 °C / 760 Torr View Scheme

1: I2 / tetrahydrofuran / 0.17 h 2: 90 percent / NaN3, NaH / dimethylformamide / 6 h / 23 °C 3: H2 / 10percent Pd/C / ethanol / 12 h / 23 °C / 760 Torr View Scheme