sodium hydride in tetrahydrofuran; N,N-dimethyl-formamide T=24°C; 0.416667 h;

potassium carbonate; N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide in N,N-dimethyl-formamide T=24°C; 20 h;

1: 42 percent / N-bromosuccinimide, H2SO4 / tetrahydrofuran / 10 h / -78 °C 2: 85 percent / dioxane / 10 h / 105 °C 3: 68 percent / NaH / tetrahydrofuran; dimethylformamide / 3 h / 25 °C 4: 91 percent / Bu3SnH, AIBN / benzene / 3 h / 80 °C 5: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h 6: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C 7: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr 8: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C 9: 71 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, K2CO3 / dimethylformamide / 20 h / 24 °C View Scheme

1: 85 percent / dioxane / 10 h / 105 °C 2: 68 percent / NaH / tetrahydrofuran; dimethylformamide / 3 h / 25 °C 3: 91 percent / Bu3SnH, AIBN / benzene / 3 h / 80 °C 4: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h 5: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C 6: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr 7: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C 8: 71 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, K2CO3 / dimethylformamide / 20 h / 24 °C View Scheme

1: 68 percent / NaH / tetrahydrofuran; dimethylformamide / 3 h / 25 °C 2: 91 percent / Bu3SnH, AIBN / benzene / 3 h / 80 °C 3: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h 4: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C 5: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr 6: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C 7: 71 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, K2CO3 / dimethylformamide / 20 h / 24 °C View Scheme

1: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h 2: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C 3: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr 4: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C 5: 71 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, K2CO3 / dimethylformamide / 20 h / 24 °C View Scheme