1.1: sodium t-butanolate / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / -10 - 5 °C 2.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C 2.2: 0.25 h 3.1: hydrogen / 20 palladium(II) hydroxide on carbon / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 5.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 6.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 7.1: iodine / acetone / 2 h / 25 - 60 °C 8.1: potassium carbonate / acetone / 20 h / 55 - 60 °C 9.1: hydrogenchloride; water / methanol / 5 h / 20 - 25 °C 9.2: 25 - 30 °C / pH 10 10.1: formic acid / palladium 10 on activated carbon / 50 °C View Scheme

1.1: sodium t-butanolate / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / -10 - 5 °C 2.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C 2.2: 0.25 h 3.1: hydrogen / 20 palladium(II) hydroxide on carbon / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere View Scheme