ammonium hydroxide in methanol T=20°C; 16 h;

ammonium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide

1: 56 percent / SOCl2; NMM / dimethylformamide / 5 h / 0 - 20 °C 2: 39 percent / NBS / CCl4 / 80 °C 3: NaN3 / dimethylformamide / 20 h / 20 °C 4: 80 percent / Ph3P / tetrahydrofuran; H2O / 20 h / 20 °C View Scheme

4-methyl-morpholine; thionyl chloride in N,N-dimethyl-formamide T=0 - 20°C; 5 h;

1.1: Lawesson's reagent / toluene / 2 h / Reflux 2.1: ethanol / 2 h / Reflux 3.1: selenium(IV) oxide / acetic acid / 12 h / Reflux 4.1: tetrahydrofuran / 0.5 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 6.1: ammonium acetate / 12 h / Reflux 7.1: potassium carbonate / ethanol; dichloromethane 8.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C 9.1: lithium hydroxide hydrate / tetrahydrofuran; water / 2 h 10.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 3 h / Inert atmosphere 11.1: BOP-Cl; triethylamine / acetonitrile / 3 h 12.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h 15.1: Dess-Martin periodane / dichloromethane / 2 h 16.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water / 2 h 16.2: pH 2 17.1: BOP-Cl; triethylamine / acetonitrile / Inert atmosphere 18.1: lithium hydroxide hydrate / tetrahydrofuran; water / 2 h / 20 °C 18.2: pH 3 19.1: dichloromethane / 2 h / 20 °C 20.1: diphenyl phosphoryl azide / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme