Multi-step reaction with 12 steps
1.1: hydrogen / palladium on activated charcoal / tetrahydrofuran / 2 h / 2068.65 Torr
2.1: sodium hydrogencarbonate / water; acetone / 20 °C / Ice bath
3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C
3.2: -78 - 20 °C
4.1: triethylamine / dichloromethane / 20 °C / Ice bath
5.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C
6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 14 h / 20 °C / 760.05 Torr
7.1: pyridine / 2.5 h / 0 - 20 °C / Inert atmosphere
8.1: water; toluene-4-sulfonic acid / acetone / 3 h / Reflux
9.1: sodium tetrahydroborate / tetrahydrofuran / Ice bath
10.1: triethylamine / dichloromethane / 20 °C / Ice bath
11.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C
12.1: hydrogen / palladium on activated charcoal / ethyl acetate / 14 h / 20 °C / 760.05 Torr
With
pyridine; sodium tetrahydroborate; n-butyllithium; sodium azide; water; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;