1: hydrogenchloride; water / acetonitrile / 4 h / -10 °C 2: sodium tetrahydroborate; diethyl methoxy borane; methanol / ethyl acetate; tetrahydrofuran / 5 h / -80 - -75 °C / Inert atmosphere View Scheme

1.1: diisobutylaluminium hydride / toluene / 2 h / -60 - -50 °C / Inert atmosphere 1.2: 0.5 h / -50 - 30 °C 2.1: manganese(IV) oxide / toluene / 24 h / 25 - 30 °C 3.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -35 - -15 °C 3.2: 1 h / -80 - -75 °C 4.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 - 30 °C 4.2: pH 1.5 - 2 4.3: 20 °C 5.1: hydrogenchloride; water / dichloromethane / 0 - 30 °C / pH 2 - 2.5 6.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 °C / Inert atmosphere 6.2: 0.5 h / 60 - 65 °C 6.3: 0.5 h / 60 - 65 °C 7.1: dichloromethane / 3.25 h / 15 - 20 °C 8.1: zinc oxide / toluene / 2 h / 25 - 30 °C / Inert atmosphere 8.2: 12 h 9.1: hydrogenchloride; water / acetonitrile / 4 h / -10 °C 10.1: sodium tetrahydroborate; diethyl methoxy borane; methanol / ethyl acetate; tetrahydrofuran / 5 h / -80 - -75 °C / Inert atmosphere View Scheme

1473 Purification / work up;