1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Reflux 2: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C 3: sodium dihydrogenphosphate; sodium chlorite; water / methyl-2-butene; tert-butyl alcohol / 1.5 h / 0 - 20 °C 4: palladium 10 on activated carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr View Scheme

1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Reflux 2: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C 3: sodium dihydrogenphosphate; sodium chlorite; water / methyl-2-butene; tert-butyl alcohol / 1.5 h / 0 - 20 °C View Scheme

sodium tetrahydroborate in methanol T=0°C; 0.5 h; Reflux;