potassium carbonate in N,N-dimethyl-formamide T=20°C; 18 h;

potassium carbonate in N,N-dimethyl-formamide T=80 - 100°C; 4 h;

in N,N-dimethyl-formamide

1: NaSEt / dimethylformamide / Heating 2: K2CO3 / acetone / Heating View Scheme

1: hydroxylamine hydrochloride; pyridine / 16 h / 120 °C 2: pyridine / 16 h / 20 °C 3: potassium ethanolate / ethanol; benzene / 5 h / 0 °C / |Inert atmosphere 4: sodium tetrahydroborate / methanol / 3 h / 20 °C 5: sodium hydroxide / dichloromethane / 3 h / 0 - 20 °C 6: sodium hydride / tetrahydrofuran; acetonitrile; mineral oil 7: lithium aluminium tetrahydride / 5 °C / |Reflux 8: 5 palladium on charcoal; hydrogen / methanol / 16 h 9: CHIRALPAK AD-H column / |Resolution of racemate 10: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C 11: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C 12: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C View Scheme

1: hydroxylamine hydrochloride; pyridine / 16 h / 120 °C 2: pyridine / 16 h / 20 °C 3: potassium ethanolate / ethanol; benzene / 5 h / 0 °C / |Inert atmosphere 4: sodium tetrahydroborate / methanol / 3 h / 20 °C 5: sodium hydroxide / dichloromethane / 3 h / 0 - 20 °C 6: sodium hydride / tetrahydrofuran; acetonitrile; mineral oil 7: lithium aluminium tetrahydride / 5 °C / |Reflux 8: 5 palladium on charcoal; hydrogen / methanol / 16 h 9: CHIRALPAK AD-H column / |Resolution of racemate 10: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C 11: pyridine / 3 h / 0 - 25 °C View Scheme