triethylamine T=20°C; 2 h;

sodium hydride in N,N-dimethyl-formamide T=20°C; 0.5 h;

in diethyl ether

nitric acid

hydrazine hydrate in ethanol 0.25 h;

1: 79 percent / NaOH / ethanol; dioxane / 2 h / Ambient temperature 2: tionyl chloride / 3 h / Heating View Scheme

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: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature View Scheme

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: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 4: 71 percent / N,N'-dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature View Scheme

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: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 5: TFA / CH2Cl2 6: EDC / dimethylformamide / 40 °C 7: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 8: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 9: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

sodium hydroxide in 1,4-dioxane; ethanol 2 h; Ambient temperature;