sodium tetrahydroborate in methanol T=0 - 20°C; 2 h;

1.1: sodium tetrahydroborate; methanol 2.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 3.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 4.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 5.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 6.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 7.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 8.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 8.2: 8 h / 50 °C / Reflux 9.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 10.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 10.2: Inert atmosphere View Scheme

1: sodium tetrahydroborate; methanol 2: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 3: sodium iodide / acetonitrile / Inert atmosphere; Reflux View Scheme