Multi-step reaction with 9 steps
1: 80 percent / butylamine / toluene / 26 h / Heating
2: 1.) H2, 2.) sodium metabisulfite / 1.) 10percent Pd/C / 1.) acetic acid, ethyl acetate, 67 h, 2.) 60percent aqueous ethanol, reflux, 3 h
3: 20 percent / titanium(IV) chloride / CH2Cl2 / 0.25 h / -10 °C
4: sodium hydrogen carbonate / dimethylformamide / 23.5 h
5: 75 percent / sodium hydrogen carbonate / dimethylformamide / 25 h / Ambient temperature
6: 1.) sulfamic acid, 2.) sodium chlorite / 1.) dioxan, 2.) dioxan, water, r.t., 2 h
7: H2 / 10percent Pd/C / ethyl acetate / 18 h
8: sodium hydrogen carbonate / dimethylformamide / 23.5 h / Ambient temperature
9: 67 percent / N,N-dicyclohexylcarbodiimide / toluene / Ambient temperature
With
sodium chlorite; sodium disulfite; aminosulfonic acid; hydrogen; titanium tetrachloride; sodium hydrogencarbonate; N-butylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1071/ch9960917