1: H2 / Ni-raney / ethanol / 12 h / 50 °C 2: 84 percent / CH2Cl2 / 12 h / Heating 3: 93 percent / aq. NaOH / methanol / 18 h / Heating 4: dicyclohexylcarbodiimide, dimethylaminopyridine / CH2Cl2 / 4 h 5: 86 percent / aq. NaOH / methanol / 72 h / Heating View Scheme

1: N-Methyl-4-nitropyrrole-2-carboxylic Acid Methyl Ester With hydrogen; palladium 10 on activated carbon in ethyl acetate T=20°C; 12 h; 2: 4-[[(tert-Butyloxy)carbonyl]-amino]-1-methylpyrrole-2-carboxylic acid With 4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethyl-formamide T=20°C; 3 h;

1: H2 / Ni-raney / ethanol / 12 h / 50 °C 2: 84 percent / CH2Cl2 / 12 h / Heating 3: 93 percent / aq. NaOH / methanol / 18 h / Heating 4: dicyclohexylcarbodiimide, dimethylaminopyridine / CH2Cl2 / 4 h View Scheme

hydrogen; palladium on activated charcoal in methanol 3 h; Ambient temperature;

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

1: H2 / Ni-raney / ethanol / 12 h / 50 °C 2: 84 percent / CH2Cl2 / 12 h / Heating 3: 93 percent / aq. NaOH / methanol / 18 h / Heating 4: 1.) aq. Cs2CO2 / 1) H2O, EtOH; 2) DMF, 40 deg C, overnight 5: TFA / CH2Cl2 / 1 h 6: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH2Cl2, 1 h; 2) CH2Cl2, 2 h, 0 deg C, 20 deg C (15 h) 7: 95 percent / H2 / Pd/C / ethanol / 12 h 8: 59 percent / TFA, EDC / dimethylformamide / Ambient temperature 9: 77 percent / H2 / Pd/C / dimethylformamide / 6 h / Ambient temperature View Scheme

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 3: 67 percent / EDCl / dimethylformamide / 1 h 4: dimethylformamide / 4 h / 55 °C View Scheme

1: NaOH / tetrahydrofuran; methanol / 20 °C 2: 82 percent / H2SO4 / diethyl ether / 36 h / 20 °C View Scheme

1: 92 percent / aq. NaOH / Heating 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: Hunig's base / tetrahydrofuran / -20 - 20 °C 4: H2 / 10percent Pd/C / methanol View Scheme