Multi-step reaction with 10 steps
1.1: hydrogen / palladium 10% on activated carbon / methanol / 20 h / 25 °C / 1551.49 Torr
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 °C / Reflux
2.2: 0 °C
3.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C
4.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C
4.2: 1 h / -78 °C
5.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
6.2: 1.5 h / -78 °C
7.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 2 h / 100 °C / Microwave irradiation
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C
9.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 50 °C / 2585.81 Torr
10.1: Daicel IB-H / ethanol; hexanes / 25 °C / Resolution of racemate
With
lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; Dess-Martin periodane; pyridinium chlorochromate; lithium hexamethyldisilazane; lithium diisopropyl amide;
bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; water;