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: 66 percent / aq. HOAc / 4 h / 45 °C
5: 53 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 24 h / 0 - 23 °C
6: 94 percent / H2 / 10percent Pd/C / ethyl acetate / 24 h / 2585.7 Torr
7: 1-hydroxybenzotriazole-benzotriazolyltetramethyluronium hexafluorophosphate, diisopropylethylamine / dimethylformamide / 24 h
With
sodium hydroxide; sulfuric acid; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium nitrite; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm00031a018