Multi-step reaction with 9 steps
1: 60 percent / 1N aq. NaOH / dioxane / 2 h / Ambient temperature
2: 77 percent / imidazole / dimethylformamide / 9 h / Ambient temperature
3: 1.) ClCO2Et, Et3N / 1.) ether, 0 deg C, 1 h, 2.) ether, RT, 7 h
4: 50 percent / silver benzoate, Et3N / 0.05 h / 80 °C
5: 60 percent / 2,6-lutidine, tert-butyldimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 3 h / 0 °C
6: 94 percent / 1-hydroxybenzotriazole hydrate, DCC / tetrahydrofuran / 5 h / 0 °C
7: 82 percent / 2,6-lutidine, TBSOTf / CH2Cl2 / 2 h / Ambient temperature
8: 95 percent / Et3N / CH2Cl2 / 5 h / Ambient temperature
9: 63 percent / 2,6-lutidine, TBSOTf / CH2Cl2 / 2 h / Ambient temperature
With
1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; t-butyldimethylsiyl triflate; silver benzoate; chloroformic acid ethyl ester; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3987/COM-94-S(B)52