1: 85.2 percent / Et3N / tetrahydrofuran / 18 h / Heating 2: BH3*SMe2 / tetrahydrofuran / 2.5 h / Heating 4: LAH View Scheme

1.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 6 h / 0 - 20 °C 2.1: diisobutylaluminium hydride / dichloromethane / 1 h / -45 °C / |Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C 3.2: 1 h / 20 °C 4.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 °C 4.2: 3.5 h / 0 °C 5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 6.1: water; tetrahydrofuran / 3 h / 65 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C View Scheme

1.1: diisobutylaluminium hydride / dichloromethane / 1 h / -45 °C / |Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C 2.2: 1 h / 20 °C 3.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 °C 3.2: 3.5 h / 0 °C 4.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: water; tetrahydrofuran / 3 h / 65 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C 1.2: 1 h / 20 °C 2.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 °C 2.2: 3.5 h / 0 °C 3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 4.1: water; tetrahydrofuran / 3 h / 65 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C View Scheme

1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 2: water; tetrahydrofuran / 3 h / 65 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C View Scheme

1: water; tetrahydrofuran / 3 h / 65 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C View Scheme

triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran T=20°C; Mitsunobu Displacement;

1: 95 percent / CH2Cl2 / 2 h / Heating 2: 84.4 percent / PPh3, diethyl azodicarboxylate / diethyl ether / 5 h / -10 °C 3: 88.7 percent / HCl gas / ethanol / Ambient temperature View Scheme

1: 95 percent / CH2Cl2 / 2 h / Heating 2: 88 percent / PPh3, diethyl azodicarboxylate / diethyl ether / 5 h / -10 °C 3: HCl / ethanol / Ambient temperature View Scheme

1.1: sodium hydride / isobutyramide 2.1: human cytochrome P450 2C19 / 0.05 h / 37 °C / aq. phosphate buffer; Enzymatic reaction 2.2: aq. phosphate buffer View Scheme