hydrogen; palladium on activated charcoal in ethanol T=30°C; 13 h;

hydrogen; rhodium on alumina in water P=775.7 Torr; 3 h;

hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol 10 h; Ambient temperature;

hydrogenchloride; palladium hydroxide on carbon 20; hydrogen in methanol P=760.051 Torr; 48 h;

hydrogen; acetic acid; palladium 18 h;

trifluoroacetic acid in water 48 h; Ambient temperature;

1: 1.) caesium acetate, 2.) K2CO3, MeOH / 1.) DMF, 40-50 deg C, 24 h, 2.) 20 deg C, 1 h 2: 1.) benzoic acid, Ph3P, diethyl azodicarboxylate, 2.) K2CO3, MeOH / 1.) THF, 0 deg C, 15 h, 2.) 20 deg C, 5 h 3: 100 percent / H2, AcOH / Pd black / 18 h View Scheme

1: NEt3 / CH2Cl2 / 0.17 h / 0 °C 2: 1.) caesium acetate, 2.) K2CO3, MeOH / 1.) DMF, 40-50 deg C, 24 h, 2.) 20 deg C, 1 h 3: 100 percent / H2, AcOH / Pd black / 18 h View Scheme

1: Et3N / CH2Cl2 / 2 h / 0 °C 2: 94 percent / 8 h / 135 °C 3: 98 percent / conc.HCl / methanol / 48 h / Ambient temperature 4: 86 percent / H2, conc.HCl / 5percent Pd/C / ethanol / 10 h / Ambient temperature View Scheme

1: 1.) triphenylphosphine, diisopropyl diazodicarboxylate / 1.) toluene, 0 deg C, 30 min, 2.) 130 deg C, 0.01 mmHg, 2.5 h 2: 67 percent / aq. HClO4 / 4 h / 20 °C 3: 1.) PhCO2H, DEAD, Ph3P, 2.) K2CO3, MeOH / 1.) THF, 0 deg C, 10 min, 2.) 20 deg C, 45 min 4: NEt3 / CH2Cl2 / 0.17 h / 0 °C 5: 1.) caesium acetate, 2.) K2CO3, MeOH / 1.) DMF, 40-50 deg C, 24 h, 2.) 20 deg C, 1 h 6: 100 percent / H2, AcOH / Pd black / 18 h View Scheme