Multi-step reaction with 14 steps
1.1: thionyl chloride / 77 h / 0 - 20 °C / Inert atmosphere; Reflux
2.1: triethylamine / dichloromethane / 5.25 h / 0 °C / Inert atmosphere; Reflux
3.1: triethylamine / dichloromethane / 14 h / 0 °C / Inert atmosphere
4.1: tetrabutylammoniun azide / acetonitrile / 1 h / 70 °C / Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere
6.1: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere
7.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 8 h / 0 - 100 °C / Inert atmosphere; Microwave irradiation
7.2: 1 h / 20 °C / Inert atmosphere; Microwave irradiation
8.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere
9.1: sodium hydrogencarbonate / water; 1,4-dioxane / 1 h / 0 - 20 °C / Inert atmosphere
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 0 - 20 °C / Inert atmosphere
11.1: diethylamino-sulfur trifluoride / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
12.1: hydrogenchloride / water; 1,4-dioxane / 1 h / 0 - 20 °C / Inert atmosphere
13.1: triethylamine / dichloromethane / 0.08 h / -20 °C / Inert atmosphere
14.1: piperidine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
With
piperidine; hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; hydrogen; tetrabutylammoniun azide; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.201302423