Multi-step reaction with 7 steps
1: 1.) NaNO2, H2SO4 2.) aq. NaOH / 1.) water, from 0 deg C to 23 deg C, 5 h, 2.) methanol, 5 min
2: dimethylformamide / 18 h / 23 °C
3: 1.) trifluoromethanesulfonic anhydride, 1,8-bis(dimethylamino)naphthalene / 1.) CH2Cl2, 0 deg C, 30 min, 2.) CH2Cl2, dioxane, 21 deg C, 15 h
4: 100 percent / H2 / 10percent Pd/C / ethanol / 2 h / 2068.6 Torr
5: 43 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / dimethylformamide / 15 h / 21 °C
6: 91 percent / aq. HOAc / 15 h / 5 °C
7: 35 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 16 h / 23 °C
With
sodium hydroxide; sulfuric acid; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; acetic acid; 1-hydroxybenzotriazol-hydrate; trifluoromethanesulfonic acid anhydride; dicyclohexyl-carbodiimide; triphenylphosphine; sodium nitrite; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jm00031a018