1: 83 percent / 5 percent aq. sulfuric acid / 8 h / 75 - 80 °C 2: 82 percent / (R,R)-diethyl tartrate, titanium tetra iso-propoxide, tert-butyl hydroperoxide / CH2Cl2 / 24 h / -23 °C 3: 100 percent / hydrogen / 5 percent Pd/C / ethanol / 19 h / 20 °C 4: 87 percent / pyridine / 14.5 h / 0 °C 5: 8 percent / lithium aluminum hydride / diethyl ether / 3 h / 21 °C View Scheme

hydrogen; platinum oxyde in ethanol T=20°C; P=750.06 Torr; 24 h;

1: 62 percent / 80 percent meta-chloroperoxybenzoic acid / CH2Cl2 / 5 h / Heating 2: 99 percent / hydrogen / 5 percent Pd/CaCO3 / ethanol / 46 h / Ambient temperature View Scheme

1.1: methanesulfonic acid / water; tetrahydrofuran / 65 - 70 °C / Inert atmosphere 2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0 - 5 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 12 h / 80 - 85 °C / Inert atmosphere 3.2: 50 - 60 °C / pH 0.1 - 0.5 / Inert atmosphere 4.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0 - 5 °C 2.1: potassium carbonate / acetonitrile / 12 h / 20 - 85 °C 2.2: 50 - 60 °C / pH 0.1 - 0.5 3.1: hydrogen / palladium 10 on activated carbon / methanol / 20 °C / 3677.86 Torr View Scheme

Jone's reagent in acetone T=0°C; 0.5 h;

1: 62 percent / 80 percent meta-chloroperoxybenzoic acid / CH2Cl2 / 5 h / Heating 2: 99 percent / hydrogen / 5 percent Pd/CaCO3 / ethanol / 46 h / Ambient temperature 3: 80 percent / hydrogen / 10 percent Pd/C / ethanol / 24 h / 60 °C View Scheme