1: With L-Selectridereg; in tetrahydrofuran 3.5 h; Inert atmosphereLarge scale; 2: With hydrogen bromide in tetrahydrofuran; ethanol T=20°C; 0.5 h; Large scale;

1: With cerium(III) chloride heptahydrate in methanol; dichloromethane T=-55 - -50°C; Luche Cerium Reduction; 0.5 h; 2: With sodium tetrahydroborate in methanol; dichloromethane T=-55 - -50°C; Luche Cerium Reduction; 2.5 h; Temperature; diastereoselective reaction;

hydrogen bromide in methanol; water T=25 - 30°C; 3 h; Product distribution / selectivity;

1: With (2S,3S)-(+)-di-O-(p-toluoyl)-tartaric acid in methanol T=20 - 35°C; 22 - 27 h; Resolution of racemateHeating / reflux; 2: With methanol; water; hydrogen bromide T=0 - 30°C; 3.5 h; Purification / work up;

1: With ammonia in dichloromethane; water T=5 - 10°C; pH=8.9 - 9.1; 2: With hydrogen bromide in ethanol; dichloromethane; water T=30 - 35°C; 3: With hydrogen bromide in ethanol; water T=0 - 5°C; pH=2.5 - 3.0; 3 h; Product distribution / selectivity;

1.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 2.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 3.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 3.2: 0.25 h / |Large scale 3.3: 0.33 h / 60 °C / pH < 1 / |Large scale 4.1: triethylamine / ethanol / |Reflux; |Large scale 5.1: L-Selectridereg; / tetrahydrofuran / 3.5 h / |Inert atmosphere; |Large scale 5.2: 0.5 h / 20 °C / |Large scale View Scheme

1.1: sulfuric acid / 6 h / 90 °C / |Inert atmosphere; |Large scale 2.1: ethanol / 4 h / |Reflux; |Large scale 3.1: sodium hydroxide; sodium tetrahydroborate / water / 1 h / 20 °C / |Large scale 4.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 5.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 6.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 7.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 7.2: 0.25 h / |Large scale 7.3: 0.33 h / 60 °C / pH < 1 / |Large scale 8.1: triethylamine / ethanol / |Reflux; |Large scale 9.1: L-Selectridereg; / tetrahydrofuran / 3.5 h / |Inert atmosphere; |Large scale 9.2: 0.5 h / 20 °C / |Large scale View Scheme

1.1: bromine / methanol / 5 - 40 °C / |Large scale 2.1: sulfuric acid / 6 h / 90 °C / |Inert atmosphere; |Large scale 3.1: ethanol / 4 h / |Reflux; |Large scale 4.1: sodium hydroxide; sodium tetrahydroborate / water / 1 h / 20 °C / |Large scale 5.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 6.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 7.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 8.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 8.2: 0.25 h / |Large scale 8.3: 0.33 h / 60 °C / pH < 1 / |Large scale 9.1: triethylamine / ethanol / |Reflux; |Large scale 10.1: L-Selectridereg; / tetrahydrofuran / 3.5 h / |Inert atmosphere; |Large scale 10.2: 0.5 h / 20 °C / |Large scale View Scheme

1.1: ethanol / 4 h / |Reflux; |Large scale 2.1: sodium hydroxide; sodium tetrahydroborate / water / 1 h / 20 °C / |Large scale 3.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 4.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 5.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 6.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 6.2: 0.25 h / |Large scale 6.3: 0.33 h / 60 °C / pH < 1 / |Large scale 7.1: triethylamine / ethanol / |Reflux; |Large scale 8.1: L-Selectridereg; / tetrahydrofuran / 3.5 h / |Inert atmosphere; |Large scale 8.2: 0.5 h / 20 °C / |Large scale View Scheme

1.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 2.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 3.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 4.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 4.2: 0.25 h / |Large scale 4.3: 0.33 h / 60 °C / pH < 1 / |Large scale 5.1: triethylamine / ethanol / |Reflux; |Large scale 6.1: L-Selectridereg; / tetrahydrofuran / 3.5 h / |Inert atmosphere; |Large scale 6.2: 0.5 h / 20 °C / |Large scale View Scheme