Multi-step reaction with 14 steps
1: 58 percent / NaH / dimethylformamide; paraffin / 4 h / Ambient temperature
2: H2 / Raney-Ni / ethanol / 2.5 h / 40 °C
3: 30 percent / Et3N / CH2Cl2 / 1 h / Ambient temperature
4: aq. NaOH / ethanol / 1 h / Ambient temperature
5: 87 percent / DCC / CH2Cl2 / Ambient temperature
6: 95 percent / 4N HCl / dioxane / 1.5 h / Ambient temperature
7: 78 percent / Et3N / CH2Cl2 / Ambient temperature
8: 63 percent / PCl5, I2, Br2 / CH2Cl2 / 1.5 h / Ambient temperature
9: 25 percent / NaN3 / dimethylformamide / 4 h / 60 °C
10: NaH / dimethylformamide; paraffin
11: H2 / Pd-C / ethanol
12: 40 percent / Et3N / CH2Cl2
13: 75 percent / 4N HCl / dioxane / Ambient temperature
14: 95 percent / 1N NaOH
With
hydrogenchloride; sodium hydroxide; sodium azide; phosphorus pentachloride; hydrogen; bromine; iodine; sodium hydride; triethylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal; nickel;
In
1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jm00397a027