1: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. 2: 94 percent / 12N HCl / 0 °C 3: 1N HCl / 3 h / Heating View Scheme

1: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. 2: 94 percent / 12N HCl / 0 °C 3: 1N HCl / 3 h / Heating 4: 90 percent / Et3N / 1,2-dimethoxy-ethane / 15 h / Ambient temperature View Scheme

sodium methylate in ethylene glycol dimethyl ether; dichloromethane; water

sodium methylate 1.) DMF, RT, 1 h, 2.) DMF, 120 deg C, 6 h; Yield given. Multistep reaction;

sodium tetrahydroborate 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min.; Yield given. Multistep reaction;

1: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. 2: 94 percent / 12N HCl / 0 °C View Scheme