N-ethyl-N,N-diisopropylamine in acetonitrile 4 h; Heating;

pyridine hydrochloride Heating;

1: CHIRALPAK AD-H column / |Resolution of racemate 2: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C 3: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C View Scheme

1: AlCl3, aluminium chloride / toluene / 1 h / 110 °C / |Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / |Inert atmosphere 3: hydroxylamine hydrochloride; pyridine / 16 h / 120 °C 4: pyridine / 16 h / 20 °C 5: potassium ethanolate / ethanol; benzene / 5 h / 0 °C / |Inert atmosphere 6: sodium tetrahydroborate / methanol / 3 h / 20 °C 7: sodium hydroxide / dichloromethane / 3 h / 0 - 20 °C 8: sodium hydride / tetrahydrofuran; acetonitrile; mineral oil 9: lithium aluminium tetrahydride / 5 °C / |Reflux 10: 5 palladium on charcoal; hydrogen / methanol / 16 h 11: CHIRALPAK AD-H column / |Resolution of racemate 12: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C 13: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C 14: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / |Inert atmosphere 2: hydroxylamine hydrochloride; pyridine / 16 h / 120 °C 3: pyridine / 16 h / 20 °C 4: potassium ethanolate / ethanol; benzene / 5 h / 0 °C / |Inert atmosphere 5: sodium tetrahydroborate / methanol / 3 h / 20 °C 6: sodium hydroxide / dichloromethane / 3 h / 0 - 20 °C 7: sodium hydride / tetrahydrofuran; acetonitrile; mineral oil 8: lithium aluminium tetrahydride / 5 °C / |Reflux 9: 5 palladium on charcoal; hydrogen / methanol / 16 h 10: CHIRALPAK AD-H column / |Resolution of racemate 11: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C 12: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C 13: 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: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C 12: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C View Scheme

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

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

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