hydrogenchloride; sodium chloride in tetrahydrofuran

1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2: cerium(III) chloride / tetrahydrofuran / 0 - 5 °C View Scheme

1: With N-ethyl-N,N-diisopropylamine; B-chloro-diisopinocampheylborane in dichloromethane T=-5 - 0°C; 3.75 - 4.75 h; 2: With triethanolamine in dichloromethane T=20 - 30°C; 2 h;

formic acid; caesium carbonate in N,N-dimethyl-formamide T=40°C; 24 h; Product distribution / selectivity;

1.1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2.1: cerium(III) chloride / tetrahydrofuran / 0 - 5 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 5.1: water; sodium hydroxide / tetrahydrofuran; methanol / 2 h / 25 - 30 °C 6.1: hydrogenchloride / water / 25 - 30 °C / pH 6.5 - 7 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 7.2: 1.5 h / 0 - 5 °C 8.1: n-butyllithium / tetrahydrofuran; hexane / -15 - 0 °C / Inert atmosphere 8.2: 19 h / -5 - 2 °C / Inert atmosphere 9.1: ethyl acetate / 15 h / 25 - 30 °C / Inert atmosphere 10.1: sulfuric acid; water / 2 h / 0 - 10 °C / Inert atmosphere 11.1: ethyl acetate / 18 h / 25 - 30 °C / Inert atmosphere 12.1: acetic acid / dichloromethane; water / 0.5 h / pH 3.5 - 4 12.2: 0.5 h / 25 - 30 °C View Scheme

in tetrahydrofuran; methanol; water

1.1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2.1: cerium(III) chloride / tetrahydrofuran / 0 - 5 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 5.1: water; sodium hydroxide / tetrahydrofuran; methanol / 25 - 30 °C 6.1: hydrogenchloride / water; ethyl acetate / 25 - 30 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 7.2: 1 h / 0 - 5 °C 8.1: sodium methylate / methanol; N,N-dimethyl-formamide / 0 - 5 °C 9.1: ethyl acetate / 25 - 30 °C 10.1: sulfuric acid; water / 5 - 10 °C View Scheme

1.1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2.1: cerium(III) chloride / tetrahydrofuran / 0 - 5 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 5.1: water; sodium hydroxide / tetrahydrofuran; methanol / 25 - 30 °C 6.1: hydrogenchloride / water; ethyl acetate / 25 - 30 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 7.2: 1 h / 0 - 5 °C 8.1: sodium methylate / methanol; N,N-dimethyl-formamide / 0 - 5 °C 9.1: ethyl acetate / 25 - 30 °C 10.1: sulfuric acid; water / 5 - 10 °C 11.1: ethyl acetate / 25 - 30 °C 12.1: acetic acid / dichloromethane; water / 25 - 30 °C 12.2: 25 - 30 °C View Scheme

1.1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2.1: cerium(III) chloride / tetrahydrofuran / 0 - 5 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 5.1: water; sodium hydroxide / tetrahydrofuran; methanol / 25 - 30 °C 6.1: hydrogenchloride / water; ethyl acetate / 25 - 30 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 7.2: 1 h / 0 - 5 °C 8.1: sodium methylate / methanol; N,N-dimethyl-formamide / 0 - 5 °C 9.1: ethyl acetate / 25 - 30 °C 10.1: sodium methylate / methanol; N,N-dimethyl-formamide / 26 h / 25 - 45 °C 11.1: sulfuric acid; water / 2.5 h / 0 - 10 °C / Inert atmosphere View Scheme

1.1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 5 °C 3.1: sodium methylate / methanol; N,N-dimethyl-formamide / 1.5 h / -5 - 0 °C 3.2: 19 h / 0 - 5 °C 4.1: tetrahydrofuran / 9 h / 0 - 5 °C View Scheme