ammonium cerium(IV) nitrate in water; acetonitrile T=20°C; Dealkylation; 3 h;

1: p-toluenosulfonic acid / CH2Cl2 / 15 h / 20 °C 2: 291 mg / H2O / Raney nickel / ethanol / 5 h / 20 °C 3: 61 percent / ceric ammonium nitrate; water / acetonitrile / 2 h / 20 °C View Scheme

1: aluminum amalgam; H2O / tetrahydrofuran / 3 h / 20 °C 2: p-toluenosulfonic acid / CH2Cl2 / 15 h / 20 °C 3: 291 mg / H2O / Raney nickel / ethanol / 5 h / 20 °C 4: 61 percent / ceric ammonium nitrate; water / acetonitrile / 2 h / 20 °C View Scheme

1: 291 mg / H2O / Raney nickel / ethanol / 5 h / 20 °C 2: 61 percent / ceric ammonium nitrate; water / acetonitrile / 2 h / 20 °C View Scheme

1: 54 percent / triethylamine; 1-hydroxybenzotriazole; 1,3-dicyclohexylcarbodiimide / acetonitrile / 15 h / 50 °C 2: aluminum amalgam; H2O / tetrahydrofuran / 3 h / 20 °C 3: p-toluenosulfonic acid / CH2Cl2 / 15 h / 20 °C 4: 291 mg / H2O / Raney nickel / ethanol / 5 h / 20 °C 5: 61 percent / ceric ammonium nitrate; water / acetonitrile / 2 h / 20 °C View Scheme

1: pyridine / 3 h / 60 °C 2: 6.38 g / acetic anhydride; trifluoroacetic anhydride / 4 h / 100 °C 3: aluminum amalgam; water / tetrahydrofuran / 3 h / 20 °C 4: 251 mg / trifluoroacetic acid; triethylsilane / CH2Cl2 / 2 h / 0 °C 5: H2 / Pd/C / methanol / 24 h / 760 Torr 6: 700 mg / α-bromoacetophenone; triethylamine; 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C View Scheme

1: 1.11 g / acetic anhydride; trifluoroacetic anhydride / 12 h / 70 °C 2: aluminum amalgam; H2O / tetrahydrofuran / 3 h / 20 °C 3: p-toluenosulfonic acid / CH2Cl2 / 15 h / 20 °C 4: 291 mg / H2O / Raney nickel / ethanol / 5 h / 20 °C 5: 61 percent / ceric ammonium nitrate; water / acetonitrile / 2 h / 20 °C View Scheme

urea T=180°C;

triethylsilane; acetic acid; trifluoroacetic acid T=70°C; 3 h;

1: aluminum amalgam; water; acetic acid / ethanol / 3 h / Heating 2: 2.83 g / trifluoroacetic acid; acetic acid; triethylsilane / 3 h / 70 °C View Scheme