1: dimethyl sulfoxide / |Inert atmosphere 2: potassium hydroxide / water; ethanol / 90 °C / |Inert atmosphere View Scheme

1: dimethylsulfoxide / 24 h / 50 °C 2: 30percent KOH / methanol / 12 h / Heating View Scheme

1: 84 percent / sodium azide / hexamethylphosphoric acid triamide / 6 h / 55 °C 2: 97 percent / hydrogen / 10percent palladium on charcoal / methanol / 2 h View Scheme

in N,N-dimethyl-formamide T=60°C; 5 h;

in N,N-dimethyl-formamide T=60°C; 3 h; Yield given;

1.1: tetrabutylammomium bromide / isopropanol acetate / 23 h / 35 °C / Large scale reaction 2.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 3.1: AlCl3, aluminium chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction View Scheme

1.1: tetrabutylammomium bromide / isopropanol acetate / 23 h / 35 °C / Large scale reaction 2.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 3.1: AlCl3, aluminium chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C View Scheme

1.1: tetrabutylammomium bromide / isopropanol acetate / 23 h / 35 °C / Large scale reaction 2.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 3.1: AlCl3, aluminium chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: tetrabutylammomium bromide / isopropanol acetate / 23 h / 35 °C / Large scale reaction 2.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 3.1: AlCl3, aluminium chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C View Scheme