1.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C 1.2: 0.25 h 2.1: hydrogen / 20 palladium(II) hydroxide on carbon / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 6.2: pH > 8 View Scheme

1.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C 1.2: 0.25 h 2.1: hydrogen / 20 palladium(II) hydroxide on carbon / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere View Scheme