Multi-step reaction with 10 steps
1: 2,6-lutidine / tetrahydrofuran / 16 h / Ambient temperature
2: 81 percent / N2H4*H2O / 3 h / Heating
3: 48 percent / 24 h / 120 °C / 1 Torr
4: 96 percent / LiI / pyridine / 14 h / Heating
5: 84 percent / diphenyl phosphoroazidate, TEA / dioxane / 4 h / Heating
6: 53 percent / aq. LiOH*H2O / ethanol / 7 h / 0 °C
7: HOBt, EDAC / dimethylformamide / 16 h / Ambient temperature
8: dimethylformamide / 2.5 h / 120 °C
9: TBAF / tetrahydrofuran / 2 h / Ambient temperature
10: EDAC, 2,2-dichloroacetic acid / dimethylsulfoxide; toluene / 16 h / Ambient temperature
With
2,6-dimethylpyridine; dichloro-acetic acid; lithium hydroxide; TEA; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium iodide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm950684z