hydrogenchloride; water in acetonitrile 3 h; Large scale;

1.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C 1.2: 1 h / 75 °C 2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C 3.1: water; oxalic acid / methanol / 6 h / 35 °C 3.2: 2.75 h / 10 - 30 °C / pH 7 View Scheme

1.1: toluene / 0.25 h / 25 °C 1.2: 14 h / 10 - 75 °C / Inert atmosphere 1.3: 0.75 h / 0 - 25 °C / pH 2.5 2.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C 2.2: 0.75 h / 0 - 25 °C / pH 6 3.1: toluene / 5 h / 25 °C / Inert atmosphere 3.2: 3 h 3.3: 2 h / 40 °C 4.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C 5.1: water; oxalic acid / methanol / 6 h / 35 °C 5.2: 2.75 h / 10 - 30 °C / pH 7 View Scheme

1.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C 1.2: 0.75 h / 0 - 25 °C / pH 6 2.1: toluene / 5 h / 25 °C / Inert atmosphere 2.2: 3 h 2.3: 2 h / 40 °C 3.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C 4.1: water; oxalic acid / methanol / 6 h / 35 °C 4.2: 2.75 h / 10 - 30 °C / pH 7 View Scheme

1.1: toluene / 5 h / 25 °C / Inert atmosphere 1.2: 3 h 1.3: 2 h / 40 °C 2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C 3.1: water; oxalic acid / methanol / 6 h / 35 °C 3.2: 2.75 h / 10 - 30 °C / pH 7 View Scheme

1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h / 0 - 5 °C 2: phosphorus tribromide / dichloromethane / 3.17 h / 0 - 20 °C 3: dichloromethane / Reflux 4: potassium carbonate / N,N-dimethyl-formamide / 20 - 80 °C 5: (-)-10-CSA / acetonitrile; water / 4 h / 20 °C View Scheme

1: dichloromethane / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 20 - 80 °C 3: (-)-10-CSA / acetonitrile; water / 4 h / 20 °C View Scheme

1: With hydrogenchloride; water in methanol T=25°C; 2.16667 h; 2: With hydrogenchloride in dichloromethane T=0 - 25°C; pH=3; 0.916667 h;

1: (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)-heptanoic acid tert-butyl ester With hydrogenchloride in water; acetonitrile T=20°C; 3 h; 2: (R)-1-phenyl-ethyl-amine in dichloromethane T=20°C; 36 h;