1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4: hydrogenchloride; water / methanol / 1 h View Scheme

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 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: 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

1.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 1.2: 0.25 h / 10 - 30 °C 2.1: methanol / 12 h / 20 - 25 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 3.2: 3 h / 20 - 25 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 4.2: 1.5 h / -25 - -15 °C 4.3: 0.08 h 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 6.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 7.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 8.1: iodine / acetone / 2 h / 25 - 60 °C 9.1: potassium carbonate / acetone / 20 h / 55 - 60 °C 10.1: hydrogenchloride; water / methanol / 5 h / 20 - 25 °C 10.2: 25 - 30 °C / pH 10 11.1: formic acid / palladium 10 on activated carbon / 50 °C View Scheme

1.1: sodium iodide; sodium azide; 1,3,5-trishydroxybenzene / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol; BH3*Et2NPh / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 4.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 4.2: 0.25 h / 10 - 30 °C 5.1: methanol / 12 h / 20 - 25 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 6.2: 3 h / 20 - 25 °C 7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 7.2: 1.5 h / -25 - -15 °C 7.3: 0.08 h 8.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 9.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 10.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 11.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 11.2: pH > 8 View Scheme

1.1: (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol; BH3*Et2NPh / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 3.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 3.2: 0.25 h / 10 - 30 °C 4.1: methanol / 12 h / 20 - 25 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 5.2: 3 h / 20 - 25 °C 6.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 6.2: 1.5 h / -25 - -15 °C 6.3: 0.08 h 7.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 8.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 9.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 10.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 10.2: pH > 8 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 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: 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: hydrogen / 20 palladium(II) hydroxide on carbon / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 3.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 4.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 5.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 5.2: pH > 8 View Scheme

1.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 2.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 3.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 3.2: pH > 8 View Scheme