Multi-step reaction with 11 steps
1: 63.5 percent / butylamine / toluene / 27 h / Heating
2: 1.) hydrogen; 2.) sodium metabisulfite / 1.) 10percent palladium on carbon / 1.) glacial AcOH, EtOAc, 63 h; 2.) aq. EtOH, 3 h, reflux
3: 22 percent / titanium(IV) chloride / CH2Cl2 / 0.12 h / Ambient temperature
4: 25 g / sodium hydrogen carbonate / dimethylformamide / 24 h
5: 61 percent / sodium hydrogen carbonate / dimethylformamide / 23 h / Ambient temperature
6: sulfamic acid, aq. sodium chlorite / dioxane / 1.2 h / Ambient temperature
7: hydrogen / 10percent palladium on carbon / ethyl acetate / 18 h
8: sodium hydrogen carbonate / dimethylformamide / 23.5 h / Ambient temperature
9: 61 percent / dicyclohexylcarbodiimide / toluene / 1 h / Ambient temperature
10: 31 percent / 5 M HCl / methanol / Ambient temperature
11: 88 percent / hydrogen / 10percent palladium on carbon / ethyl acetate / 16 h
With
hydrogenchloride; sodium chlorite; sodium disulfite; aminosulfonic acid; hydrogen; titanium tetrachloride; sodium hydrogencarbonate; N-butylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1071/C96173