Multi-step reaction with 10 steps
1: 95 percent / H2 / 10percent Pd/C / acetic acid / 48 h / 2585.7 Torr
2: 73 percent / NaOH / dioxane / 18 h
3: 78 percent / imidazol, I2, triphenylphosphine chloride / toluene / 1.5 h
4: 27 percent / cesium carbonate / dimethylformamide / 20 h / Ambient temperature
5: 100 percent / NaOH / methanol / 16 h
6: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) EtOAc, -15 deg C, 0.5 h, 2.) EtOAc, Et2O, 0 deg C, 20 min
7: 24 percent / silver benzoate, Et3N / 0.5 h / Ambient temperature
8: H2 / 10percent Pd/C / ethanol / 12 h
9: NaHCO3 / ethyl acetate / 18 h / Ambient temperature
10: LiOH / tetrahydrofuran; methanol; H2O / 18 h
With
4-methyl-morpholine; 1H-imidazole; lithium hydroxide; sodium hydroxide; hydrogen; iodine; silver benzoate; sodium hydrogencarbonate; caesium carbonate; triethylamine; dichlorotriphenylphosphorane; isobutyl chloroformate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00042a007