Multi-step reaction with 12 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 20 °C / 760.05 Torr
2: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1 h / 0 °C / 760.05 Torr
3: pyridinium chlorochromate / dichloromethane / 24 h / 20 °C / 760.05 Torr
4: caesium carbonate / methanol; hexane / 1 h / 60 °C / 760.05 Torr
5: caesium carbonate / acetonitrile / 1.5 h / 70 °C / 760.05 Torr
6: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / 760.05 Torr / Cooling with ice
7: pyridinium chlorochromate / dichloromethane / 18 h / 20 °C / 760.05 Torr
8: zinc(II) iodide / dichloromethane / 1 h / 20 °C / 760.05 Torr / Cooling with ice
9: sulfuric acid / 18 h / 760.05 Torr / Cooling with ice; Reflux
10: perchloric acid / 0.67 h / 20 °C / 760.05 Torr
11: lithium hydroxide / tetrahydrofuran; methanol / 18 h / 60 °C / 760.05 Torr
12: formic acid / isopropyl alcohol; hexane / Resolution of racemate
With
lithium aluminium tetrahydride; formic acid; perchloric acid; sulfuric acid; caesium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) iodide; lithium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; isopropyl alcohol; toluene; acetonitrile;