triethylsilane; trifluoroacetic acid in dichloromethane

1: 83 percent / H2 / [((R)-Binap)-RuCl2]2(NEt3) / tetrahydrofuran; methanol / 17 h / 90 - 95 °C / 7500.6 Torr 2: 87 percent / DMAP; EDCl / CH2Cl2 / 16 h / 20 °C 3: 100 percent / Et3SiH; trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C View Scheme

1: 59 percent / t-BuOK / benzene / 144 h / Heating 2: 83 percent / H2 / [((R)-Binap)-RuCl2]2(NEt3) / tetrahydrofuran; methanol / 17 h / 90 - 95 °C / 7500.6 Torr 3: 87 percent / DMAP; EDCl / CH2Cl2 / 16 h / 20 °C 4: 100 percent / Et3SiH; trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C View Scheme

1: 87 percent / DMAP; EDCl / CH2Cl2 / 16 h / 20 °C 2: 100 percent / Et3SiH; trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C View Scheme

1: 87 percent / DMAP; EDCl / CH2Cl2 / 16 h / 20 °C 2: 100 percent / Et3SiH; trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C View Scheme

1: 93 percent / aq. H2O2; LiOH / tetrahydrofuran / 1 h / 0 °C 2: 87 percent / DMAP; EDCl / CH2Cl2 / 16 h / 20 °C 3: 100 percent / Et3SiH; trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C View Scheme