Multi-step reaction with 9 steps
1.1: toluene-4-sulfonic acid / toluene / 6 h / Reflux; Dean-Stark
2.1: n-butyllithium; N-cyclohexyl-cyclohexanamine / hexane; toluene / 0.08 h / 0 - 25 °C / Inert atmosphere
2.2: 1 h / Inert atmosphere
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 25 °C
4.1: sodium hydride / tetrahydrofuran / 0.17 h / 25 °C / Inert atmosphere
4.2: 1 h / 80 °C / Inert atmosphere
5.1: toluene-4-sulfonic acid / acetone / 20 °C / Inert atmosphere
6.1: ammonium acetate / ethanol / 7 h / Reflux
7.1: 2,6-dimethylpyridine / dichloromethane / 10 h / 20 °C
8.1: Resolution of racemate
9.1: hydrogenchloride / ethyl acetate / 1 h
With
2,6-dimethylpyridine; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; ammonium acetate; sodium hydride; toluene-4-sulfonic acid; N-cyclohexyl-cyclohexanamine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; acetone; toluene;