tetrabutyl ammonium fluoride in tetrahydrofuran 24 h;

ammonia; water in water T=0°C; 0.833333 h; Product distribution / selectivity;

1: 83 percent / Et3N, DMAP / pyridine / 16 h / Ambient temperature 2: 94 percent / 2 M NaOH / methanol; dioxane / 0.08 h / 0 °C 3: 18.8 g / LiN3, PPh3, DEAD / dimethylformamide / 6 h / Ambient temperature 4: 68 percent / H2 / 10percent Pd/C / ethanol; CH2Cl2 5: 98 percent / Et3N / CH2Cl2 / 16 h / Ambient temperature 6: 94 percent / TBAF / tetrahydrofuran / 24 h View Scheme

1: 90 percent / pyridine; triethylamine / dimethylformamide 2: 70 percent / pyridine View Scheme

1: 90 percent / pyridine; triethylamine / dimethylformamide 2: 70 percent / pyridine View Scheme

1: 98 percent / Et3N / CH2Cl2 / 16 h / Ambient temperature 2: 94 percent / TBAF / tetrahydrofuran / 24 h View Scheme

pyridine

chloro-trimethyl-silane in pyridine

1: N,N-dimethyl-formamide / 20 °C 2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1.5 h / 65 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1.5 h / 65 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme