Multi-step reaction with 11 steps
1.1: acetonitrile / Reflux
2.1: hydrogen / palladium on activated charcoal / tetrahydrofuran / 2 h / 2068.65 Torr
3.1: sodium hydrogencarbonate / water; acetone / 20 °C / Ice bath
4.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C
4.2: -78 - 20 °C
5.1: triethylamine / dichloromethane / 20 °C / Ice bath
6.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C
7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 14 h / 20 °C / 760.05 Torr
8.1: pyridine / 2.5 h / 0 - 20 °C / Inert atmosphere
9.1: water; toluene-4-sulfonic acid / acetone / 3 h / Reflux
10.1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 5 h / Reflux
11.1: potassium hydroxide / N,N-dimethyl-formamide / 0 °C
With
pyridine; n-butyllithium; sodium azide; hydroxylamine hydrochloride; water; hydrogen; sodium acetate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; potassium hydroxide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;