Multi-step reaction with 12 steps
1.1: thionyl chloride / 72 h / 0 - 20 °C
2.1: triethylamine / dichloromethane / 16 h / Reflux
3.1: triethylamine / dmap / dichloromethane / 24 h / 30 °C
4.1: lithium borohydride / tetrahydrofuran / 16.5 h / 0 - 30 °C
5.1: trifluoroacetic anhydride / tetrahydrofuran / 3 h / -78 °C
5.2: -78 °C / Reflux
5.3: 1 h / 20 °C
6.1: hydrogen / palladium on carbon / ethanol / 16 h / 20 °C
7.1: triethylamine / dichloromethane / 0 - 30 °C
8.1: triethylamine / dichloromethane / 0.25 h / 0 °C
9.1: sodium azide / N,N-dimethyl-formamide / 72 h / 70 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 - 20 °C
11.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C
12.1: hydrogen / tetrahydrofuran / 16 h / 20 °C
With
lithium borohydride; thionyl chloride; sodium azide; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; hydrogen; triethylamine; trifluoroacetic anhydride;
dmap; palladium on carbon;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;