1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 6: H2; aq. HCl / Pd/C / methanol View Scheme

1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 View Scheme

1.1: sodium ethanolate; sodium iodide / ethanol 2.1: potassium acetate / water; dimethyl sulfoxide 3.1: sodium hydroxide 4.1: thionyl chloride 5.1: pyridine / 12 h / 40 °C 6.1: dicyclohexyl(trifluoromethylsulfonyloxy)borane; triethylamine / -78 - 0 °C 7.1: dihydrogen peroxide; lithium hydroxide hydrate / tetrahydrofuran; water / 0.25 h 7.2: Acidic aq. solution 8.1: water; lithium hydroxide hydrate / 1,4-dioxane / 120 h / 40 °C 9.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.33 h / 20 °C 10.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 65 °C 11.1: 1.5 h / 65 °C 12.1: 2-hydroxy-pyridine / tert-butyl methyl ether / 65 °C View Scheme

sodium iodide in acetone T=20 - 56°C; 240 h;