lithium hydroxide; water in tetrahydrofuran; ethanol T=20°C;

1: 88 percent / toluene / Heating 2: 74 percent / H2 / Pd/C / methanol / 20 °C 3: 95 percent / LiOH*H2O; H2O / tetrahydrofuran; ethanol / 20 °C View Scheme

1.1: LDA; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 95 percent / tetrahydrofuran; hexane / 14 h / -78 - 20 °C 2.1: 83 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0 - 20 °C 3.1: 81 percent / PDC; celite / CH2Cl2 / 1 h / 20 °C 4.1: 88 percent / toluene / Heating 5.1: 74 percent / H2 / Pd/C / methanol / 20 °C 6.1: 95 percent / LiOH*H2O; H2O / tetrahydrofuran; ethanol / 20 °C View Scheme

1.1: 91 percent / H2SO4 / Heating 2.1: LDA; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 95 percent / tetrahydrofuran; hexane / 14 h / -78 - 20 °C 3.1: 83 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0 - 20 °C 4.1: 81 percent / PDC; celite / CH2Cl2 / 1 h / 20 °C 5.1: 88 percent / toluene / Heating 6.1: 74 percent / H2 / Pd/C / methanol / 20 °C 7.1: 95 percent / LiOH*H2O; H2O / tetrahydrofuran; ethanol / 20 °C View Scheme

1: 81 percent / PDC; celite / CH2Cl2 / 1 h / 20 °C 2: 88 percent / toluene / Heating 3: 74 percent / H2 / Pd/C / methanol / 20 °C 4: 95 percent / LiOH*H2O; H2O / tetrahydrofuran; ethanol / 20 °C View Scheme

1: 83 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0 - 20 °C 2: 81 percent / PDC; celite / CH2Cl2 / 1 h / 20 °C 3: 88 percent / toluene / Heating 4: 74 percent / H2 / Pd/C / methanol / 20 °C 5: 95 percent / LiOH*H2O; H2O / tetrahydrofuran; ethanol / 20 °C View Scheme

potassium hydroxide