2: NaBH4 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 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

copper dichloride in N,N-dimethyl-formamide T=100 - 105°C; 1.5 h;

1: 90 percent / potassium carbonate / acetone / 4 h / Heating 2: 85 percent / ammonium acetate; acetic acid / 4 h / 100 °C 3: 80 percent / sodium borohydride / ethanol / 2 h / 0 °C View Scheme

pyridine; aluminium trichloride

1: AlCl3, Py 2: NaH View Scheme

1: 83 percent / K2CO3 / acetonitrile / 20 h / 50 °C 2: 85 percent / mCPBA / CH2Cl2 / 14 h / Heating View Scheme

1.1: 83 percent / K2CO3 / acetonitrile / 20 h / 50 °C 2.1: 85 percent / mCPBA / CH2Cl2 / 14 h / Heating 3.1: NaH / tetrahydrofuran / 0.33 h 3.2: 88 percent / tetrahydrofuran / 18 h / 20 °C View Scheme