4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in N,N-dimethyl-formamide 64 h; Ambient temperature;

1: 100 percent / sodium borohydride, MeOH / 2-methyl-propan-2-ol / 0.5 h / Heating 2: 41 percent / p-TsOH*H2O / tetrahydrofuran / 0.5 h / Ambient temperature 3: 87 percent / CBr4, PPh3 / dimethylformamide / 0.5 h / 0 °C 4: 64 percent / K2CO3 / dimethylformamide / 5 h / Ambient temperature 5: 72 percent / 2.0 M HCl / 1.25 h / Heating 6: 45 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / dimethylformamide / 64 h / Ambient temperature View Scheme

1: 41 percent / p-TsOH*H2O / tetrahydrofuran / 0.5 h / Ambient temperature 2: 87 percent / CBr4, PPh3 / dimethylformamide / 0.5 h / 0 °C 3: 64 percent / K2CO3 / dimethylformamide / 5 h / Ambient temperature 4: 72 percent / 2.0 M HCl / 1.25 h / Heating 5: 45 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / dimethylformamide / 64 h / Ambient temperature View Scheme

1: 87 percent / CBr4, PPh3 / dimethylformamide / 0.5 h / 0 °C 2: 64 percent / K2CO3 / dimethylformamide / 5 h / Ambient temperature 3: 72 percent / 2.0 M HCl / 1.25 h / Heating 4: 45 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / dimethylformamide / 64 h / Ambient temperature View Scheme

1: 64 percent / K2CO3 / dimethylformamide / 5 h / Ambient temperature 2: 72 percent / 2.0 M HCl / 1.25 h / Heating 3: 45 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / dimethylformamide / 64 h / Ambient temperature View Scheme

1: 72 percent / 2.0 M HCl / 1.25 h / Heating 2: 45 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / dimethylformamide / 64 h / Ambient temperature View Scheme