1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 3: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 4: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 6: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 7: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 8: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 9: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 10: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 11: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 12: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 13: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 14: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 15: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 16: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere View Scheme

1: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 2: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 3: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 5: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 6: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 7: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 8: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 9: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 10: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 11: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 12: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 13: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 14: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 15: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere View Scheme

1: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 3: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 4: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 6: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 7: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 8: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 9: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 10: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 11: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 12: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 13: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere View Scheme

1: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 2: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 3: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 4: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere View Scheme

1: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 2: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 3: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 4: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 5: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere View Scheme

1: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature 2: 78 percent / H2S, pyridine / 1.5 h / Ambient temperature View Scheme

sulfuric acid

1: With N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide T=20°C; 96 h; 2: With sodium hydroxide in methanol; water; N,N-dimethyl-formamide 12 h; Further stages;

1: diisopropylethylamine / dimethylformamide / 96 h / Ambient temperature 2: aq. NaOH / methanol / Ambient temperature View Scheme

Amberlite IRA-400(OH-) in methanol 3 h; Ambient temperature;