triethylamine; dicyclohexyl-carbodiimide in tetrahydrofuran T=0°C; 2 h;

1.1: NaOH / 90 °C 1.2: 80 percent / H2O2 2.1: 85 percent / hydrogen / palladium catalyst / methanol / 25 °C / 2327.17 Torr 3.1: sodium nitrite; sulfuric acid / acetic acid / 0 °C 3.2: 86 percent / sodium azide / acetic acid / 0.5 h / 20 °C 4.1: 80 percent / dicyclohexylcarbodiimide; Et3N / tetrahydrofuran / 2 h / 0 °C View Scheme

1.1: 85 percent / hydrogen / palladium catalyst / methanol / 25 °C / 2327.17 Torr 2.1: sodium nitrite; sulfuric acid / acetic acid / 0 °C 2.2: 86 percent / sodium azide / acetic acid / 0.5 h / 20 °C 3.1: 80 percent / dicyclohexylcarbodiimide; Et3N / tetrahydrofuran / 2 h / 0 °C View Scheme

1.1: 78 percent / acetyl nitrate / acetonitrile / 0 - 20 °C 2.1: 100 percent / sodium acetate / 0.08 h / microwave irradiation 3.1: NaOH / 90 °C 3.2: 80 percent / H2O2 4.1: 85 percent / hydrogen / palladium catalyst / methanol / 25 °C / 2327.17 Torr 5.1: sodium nitrite; sulfuric acid / acetic acid / 0 °C 5.2: 86 percent / sodium azide / acetic acid / 0.5 h / 20 °C 6.1: 80 percent / dicyclohexylcarbodiimide; Et3N / tetrahydrofuran / 2 h / 0 °C View Scheme

1.1: 100 percent / sodium acetate / 0.08 h / microwave irradiation 2.1: NaOH / 90 °C 2.2: 80 percent / H2O2 3.1: 85 percent / hydrogen / palladium catalyst / methanol / 25 °C / 2327.17 Torr 4.1: sodium nitrite; sulfuric acid / acetic acid / 0 °C 4.2: 86 percent / sodium azide / acetic acid / 0.5 h / 20 °C 5.1: 80 percent / dicyclohexylcarbodiimide; Et3N / tetrahydrofuran / 2 h / 0 °C View Scheme

1.1: sodium nitrite; sulfuric acid / acetic acid / 0 °C 1.2: 86 percent / sodium azide / acetic acid / 0.5 h / 20 °C 2.1: 80 percent / dicyclohexylcarbodiimide; Et3N / tetrahydrofuran / 2 h / 0 °C View Scheme