Multi-step reaction with 10 steps
1: 89 percent / ethanol; diethyl ether / 1 h / 0 °C
2: H2 / 10percent Pd/C / methanol / 4 h / 760 Torr
3: 84 percent / N,N'-dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CH2Cl2 / 18 h
4: aq. sodium bicarbonate / tetrahydrofuran / 11 h
5: 86 percent / N,N'-dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CH2Cl2 / 19 h
6: 100 percent / 4 N HCl / dioxane / 4 h
7: 46 percent / pyridine / dimethylformamide / 12 h / 60 °C
8: 95 percent / methanol / 1.) 0 deg C, 30 min, 2.) RT, 12 h
9: H2 / 10percent Pd/C / methanol / 12 h / 760 Torr
10: triethylamine / dimethylformamide; dioxane / 1.) -20 deg C, 1 h, 2.) 0 deg C, 24 h
With
pyridine; hydrogenchloride; hydrogen; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00233a006