Multi-step reaction with 9 steps
1: 90 percent / toluene / 2 h / Ambient temperature
2: 20 percent / acetic anhydride / 2 h / 75 °C
3: 90 percent / 1N aq. NaOH / 0.5 h / 75 °C
4: 87 percent / H2 / 10percent Pd/C / 8 h
5: 98 percent / NaHCO3 / tetrahydrofuran; H2O; toluene / 0.5 h
6: 82 percent / NaNO2, aq. HCl / ethanol / 0.5 h / 30 °C
7: 86 percent / Na2S2O4 / ethanol; H2O / 0.5 h
8: 1.) 1-hydroxybenztriazole (1-HOBT), 1-ethyl-2-<3-(dimethylamino)propyl>carbodiimide hydrochloride (WSC*HCl), 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, CH2Cl2, RT, 4 h, 2.) THF, CH2Cl2, DMF, RT, 1 h
9: 69 percent / H2 / 10percent Pd/C / ethanol / 15 h
With
hydrogenchloride; dmap; sodium hydroxide; sodium dithionite; hydrogen; acetic anhydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; water; toluene;
DOI:10.1021/jm00069a009