1: With sodium tetrahydroborate; boron trifluoride diethyl etherate in tetrahydrofuran 2 h; Cooling with iceReflux; 2: With hydrogenchloride in ethanol; water 1 h; Reflux;

monopotassium carbonate in methanol; water T=20°C;

1: sodium hydroxide; tetrabutylammomium bromide / water; toluene / 1 h / 20 °C 2: palladium 10 on activated carbon; hydrogen / ethanol / 3 h / 20 °C / 1520.1 Torr 3: sodium hydroxide / water; methanol / 0.5 h / 20 °C 4: sulfuric acid; potassium nitrate / 20 °C 5: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 2 h / |Reflux View Scheme