manganese(IV) oxide in chloroform 24 h; Ambient temperature;

1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 110 °C / Inert atmosphere 2: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 5 h / 25 °C 3: hydrogen / palladium on carbon / ethanol / Inert atmosphere View Scheme

1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 5 h / 25 °C 2: hydrogen / palladium on carbon / ethanol / Inert atmosphere View Scheme

1: 7.2 g / LiAlH4 / tetrahydrofuran / 1 h 2: 82 percent / MnO2 / CHCl3 / 24 h / Ambient temperature View Scheme