Multi-step reaction with 7 steps
1: 1) Sodium hydride / 1.) Dioxane, 90 deg C, 2 h, 2.) 65 deg C, 6 h, 3.) ethyl acetate, ether, room temperature, 30 min.
2: 73.6 percent / Dowex 50 (H+-form) / methanol / 2 h / Reflux
3: 67 percent / Triethylamine / CH2Cl2 / 12 h / 5 °C
4: Silver trifluoromethanesulfonate / CH2Cl2 / 1) -45 deg C, 2 h, 2) -20 deg C, 1 h.
5: 0.5M-NaOH / 1) 60 deg C, 3.5 h, 2) methanol, butylamine, 85 deg C, 15 h, sealed ampoule
6: 62 percent / H2O / 2.5 h / Ambient temperature
7: 33 percent / 1) 1-Hydroxybenzotriazole, 2) N,N'-dicyclohexylcarbodiimide, triethylamine / dimethylformamide / 48 h / Ambient temperature
With
sodium hydroxide; Dowex 50 (H+-form); silver trifluoromethanesulfonate; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide;