1: With hydrogen; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; Rh(acac)2(CO)2 in tetrahydrofuran T=100°C; P=45003.6 Torr; 72 h; 2: With sulfuric acid 2 h; Heating;

hydrogenchloride; sodium tetrahydroborate; boron trifluoride diethyl etherate 1.) THF, reflux, 45 min, 2.) EtOH, reflux, 1 h; Yield given. Multistep reaction;

1.1: 84 percent / NaH / dimethylsulfoxide / 0.5 h / 20 °C 2.1: XANTHPHOS; H2 / Rh(acac)2(CO)2 / tetrahydrofuran / 72 h / 100 °C / 45003.6 Torr 2.2: 85 percent / aq. H2SO4 / 2 h / Heating View Scheme

1: 65 percent 2: 1.) sodium borohydride, boron trifluoride-etherate, 2.) 6 N HCl / 1.) THF, reflux, 45 min, 2.) EtOH, reflux, 1 h View Scheme

sodium hydroxide in methanol; dichloromethane; ammonia; water; hydrogen bromide; acetic acid