1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 2.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 2.2: 0.25 h / 10 - 30 °C 3.1: methanol / 12 h / 20 - 25 °C View Scheme

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 2.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 2.2: 0.25 h / 10 - 30 °C 3.1: methanol / 12 h / 20 - 25 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 4.2: 3 h / 20 - 25 °C 5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 5.2: 1.5 h / -25 - -15 °C 5.3: 0.08 h 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 7.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 8.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 9.1: potassium carbonate / acetone / 24 h / 25 - 60 °C 10.1: hydrogenchloride; water / methanol / 5.5 h / 20 - 55 °C 10.2: 25 - 30 °C / pH 10 View Scheme