hydrogen; palladium on activated charcoal in tetrahydrofuran 0.25 h;

hydrogenchloride in 1,4-dioxane T=90°C; 1.5 h;

1: 98 percent / NaH / dimethylformamide / a) 25 deg C, 14 h, b) 40 deg C, 4 h 2: 96 percent / H2 / 10percent Pd/C / ethanol; hexane / 24 h / 20 °C 3: 1.) NaIO4, 2.) NaBH4 / 1.) H2O, CH3OH, THF, RT, 24 h, 2.) H2O, CH3OH, THF, RT, 1.5 h View Scheme

1: 96 percent / H2 / 10percent Pd/C / ethanol; hexane / 24 h / 20 °C 2: 1.) NaIO4, 2.) NaBH4 / 1.) H2O, CH3OH, THF, RT, 24 h, 2.) H2O, CH3OH, THF, RT, 1.5 h View Scheme

1: toluene / 1 h / 80 °C 2: pyridine / CHCl3 / Ambient temperature 3: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 4: phosphorus oxychloride, Et3N, pyridine / CHCl3 / Ambient temperature 5: 66 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 6: 81 percent / pyridine / Ambient temperature 7: 99 percent / pyridine / CHCl3 / Ambient temperature 8: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 9: t-BuOK / tetrahydrofuran / Ambient temperature 10: dimethylformamide / 80 °C 11: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 12: 93.8 percent / H2 / 10percent Pd/C / tetrahydrofuran / 0.25 h View Scheme

1: 81 percent / pyridine / Ambient temperature 2: 99 percent / pyridine / CHCl3 / Ambient temperature 3: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 4: t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 7: 93.8 percent / H2 / 10percent Pd/C / tetrahydrofuran / 0.25 h View Scheme

1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl3 / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 9: 93.8 percent / H2 / 10percent Pd/C / tetrahydrofuran / 0.25 h View Scheme

1: 99 percent / pyridine / CHCl3 / Ambient temperature 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: t-BuOK / tetrahydrofuran / Ambient temperature 4: dimethylformamide / 80 °C 5: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 6: 93.8 percent / H2 / 10percent Pd/C / tetrahydrofuran / 0.25 h View Scheme

1: dimethylformamide / 80 °C 2: pyridine / CHCl3 / Ambient temperature 3: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 4: phosphorus oxychloride, Et3N, pyridine / CHCl3 / Ambient temperature 5: 66 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 6: 81 percent / pyridine / Ambient temperature 7: 99 percent / pyridine / CHCl3 / Ambient temperature 8: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 9: t-BuOK / tetrahydrofuran / Ambient temperature 10: dimethylformamide / 80 °C 11: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 12: 93.8 percent / H2 / 10percent Pd/C / tetrahydrofuran / 0.25 h View Scheme

1: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 2: 93.8 percent / H2 / 10percent Pd/C / tetrahydrofuran / 0.25 h View Scheme