1: EDC / dimethylformamide / 40 °C 2: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 3: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 4: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

hydrogen; palladium on activated charcoal in ethanol 12 h;

1: 100 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature 2: 1.) 2 M aq. NaOH / 1.) MeOH, 0 deg C, 6 h, 2.) MeOH, ether, RT, 30 min View Scheme

1M aq. NaCO3 in benzene

1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: 2.5 h / ice-bath View Scheme

in water; benzene 0.25 h;

1: 90 percent / sodium carbonate / acetone / 18 h / Heating 2: 35 percent / nitric acid, acetic anhydride / 1) -20 deg C, 6 h; 2) room temperature, 4 h 3: H2 / Ni-raney / ethanol / 12 h / 50 °C 4: 84 percent / CH2Cl2 / 12 h / Heating 5: 93 percent / aq. NaOH / methanol / 18 h / Heating 6: 1.) aq. Cs2CO2 / 1) H2O, EtOH; 2) DMF, 40 deg C, overnight 7: TFA / CH2Cl2 / 1 h 8: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH2Cl2, 1 h; 2) CH2Cl2, 2 h, 0 deg C, 20 deg C (15 h) 9: 95 percent / H2 / Pd/C / ethanol / 12 h View Scheme

1: 35 percent / nitric acid, acetic anhydride / 1) -20 deg C, 6 h; 2) room temperature, 4 h 2: H2 / Ni-raney / ethanol / 12 h / 50 °C 3: 84 percent / CH2Cl2 / 12 h / Heating 4: 93 percent / aq. NaOH / methanol / 18 h / Heating 5: 1.) aq. Cs2CO2 / 1) H2O, EtOH; 2) DMF, 40 deg C, overnight 6: TFA / CH2Cl2 / 1 h 7: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH2Cl2, 1 h; 2) CH2Cl2, 2 h, 0 deg C, 20 deg C (15 h) 8: 95 percent / H2 / Pd/C / ethanol / 12 h View Scheme

1: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH2Cl2, 1 h; 2) CH2Cl2, 2 h, 0 deg C, 20 deg C (15 h) 2: 95 percent / H2 / Pd/C / ethanol / 12 h View Scheme

1: 1.) aq. Cs2CO2 / 1) H2O, EtOH; 2) DMF, 40 deg C, overnight 2: TFA / CH2Cl2 / 1 h 3: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH2Cl2, 1 h; 2) CH2Cl2, 2 h, 0 deg C, 20 deg C (15 h) 4: 95 percent / H2 / Pd/C / ethanol / 12 h View Scheme