hydrogen; palladium on activated charcoal in methanol

1: CF3COOH / 0.25 h / Ambient temperature 2: acetonitrile / 15 h / Ambient temperature 3: CF3COOH / 0.33 h / Ambient temperature 4: acetonitrile / 15 h / Ambient temperature 5: 1.) H2, AcOH, 2.) H+ / 1.) Pd black / 1.) RT, 5 d View Scheme

1: CF3COOH / 0.33 h / Ambient temperature 2: acetonitrile / 15 h / Ambient temperature 3: 1.) H2, AcOH, 2.) H+ / 1.) Pd black / 1.) RT, 5 d View Scheme

1: 7.00 g / Et3N / H2O; dimethylformamide 2: 86.8 percent / dicyclohexylcarbodiimide (DCC) / ethyl acetate / 2 h / 0 °C 3: 70.8 percent / 25percent aq. ammonia / tetrahydrofuran / 2 h / Ambient temperature 4: CF3COOH / 0.25 h / Ambient temperature 5: acetonitrile / 15 h / Ambient temperature 6: CF3COOH / 0.33 h / Ambient temperature 7: acetonitrile / 15 h / Ambient temperature 8: 1.) H2, AcOH, 2.) H+ / 1.) Pd black / 1.) RT, 5 d View Scheme

1: 86.8 percent / dicyclohexylcarbodiimide (DCC) / ethyl acetate / 2 h / 0 °C 2: 70.8 percent / 25percent aq. ammonia / tetrahydrofuran / 2 h / Ambient temperature 3: CF3COOH / 0.25 h / Ambient temperature 4: acetonitrile / 15 h / Ambient temperature 5: CF3COOH / 0.33 h / Ambient temperature 6: acetonitrile / 15 h / Ambient temperature 7: 1.) H2, AcOH, 2.) H+ / 1.) Pd black / 1.) RT, 5 d View Scheme

1: acetonitrile / 15 h / Ambient temperature 2: 1.) H2, AcOH, 2.) H+ / 1.) Pd black / 1.) RT, 5 d View Scheme

1: acetonitrile / 15 h / Ambient temperature 2: CF3COOH / 0.33 h / Ambient temperature 3: acetonitrile / 15 h / Ambient temperature 4: 1.) H2, AcOH, 2.) H+ / 1.) Pd black / 1.) RT, 5 d View Scheme

1: 70.8 percent / 25percent aq. ammonia / tetrahydrofuran / 2 h / Ambient temperature 2: CF3COOH / 0.25 h / Ambient temperature 3: acetonitrile / 15 h / Ambient temperature 4: CF3COOH / 0.33 h / Ambient temperature 5: acetonitrile / 15 h / Ambient temperature 6: 1.) H2, AcOH, 2.) H+ / 1.) Pd black / 1.) RT, 5 d View Scheme

1: 75 percent / NaOH / dimethylformamide; H2O / 12 h 2: 77 percent / H2 / Pd/C / methanol View Scheme

hydrogen; hydrogen cation; acetic acid; palladium 1.) RT, 5 d; Yield given. Multistep reaction. Yields of byproduct given;