1.1: sodium iodide; 1,3,5-trishydroxybenzene; sodium nitrite / 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*N,N-diethylanilline / toluene / 25 - 40 °C / Inert atmosphere 3.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 4.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 4.2: 0.25 h / 30 °C 4.3: 20 - 25 °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

Multi-step reaction with 4 steps 1.1: sodium iodide; 1,3,5-trishydroxybenzene; sodium nitrite / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere2.1: dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / toluene; tetrahydrofuran / 4 h / 25 - 30 °C / Inert atmosphere3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 2 h / 0 - 10 °C4.1: hydrogenchloride; zinc / isopropyl alcohol; water / 2 h / 40 °C4.2: pH 12 - 13