Multi-step reaction with 10 steps
1: 1.) 40percentaq. AcOH, NaNO3, 2.) Al(Hg), H2O / 1.) 1,4-dioxane, 2.5 h, 2.) THF, reflux, 1 h
2: sat. aq. NaHCO3 / 12 h / Ambient temperature
3: 58 percent / LiOH*H2O / acetone; H2O / 12 h / Ambient temperature
4: 91 percent / DCC / ethyl acetate / 12 h / Ambient temperature
5: 93 percent / aq. HCl / dioxane / 0.5 h / Ambient temperature
6: NOCl / tetrahydrofuran / 0 °C
7: toluene / 0.5 h / 80 °C
8: toluene / 1 h / 80 °C
9: aq. HCl / dioxane / 0.5 h
10: Et3N, DCC / CH2Cl2 / 12 h / 0 - 20 °C
With
hydrogenchloride; lithium hydroxide; sodium nitrate; aluminum amalgam; water; sodium hydrogencarbonate; acetic acid; nitrosylchloride; triethylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; acetone; toluene;
DOI:10.1021/jm00178a012