4 Pd/C in isopropyl alcohol T=69.84°C; 4 h; Inert atmosphere;

perchloric acid; hydrogen; palladium on activated charcoal in ethanol P=3040 Torr; 48 h;

hydrogen; palladium on activated charcoal in 1,2-dichloro-ethane T=50°C; P=6000.6 Torr; 4 h;

hydrogen; palladium dihydroxide in ethyl acetate T=20°C; 22 h;

hydrogen; palladium dihydroxide in ethyl acetate T=20°C; 22 h;

hydrogen; palladium on activated charcoal in ethyl acetate

1.1: (n-Bu)2BOTf; Et3N / CH2Cl2 / 1.33 h / -78 - 0 °C 1.2: CH2Cl2 / 2 h / -78 - 0 °C 1.3: H2O2 / CH2Cl2; aq. phosphate buffer / 20 °C / pH 7.2 2.1: 3.11 g / 2,6-lutidine / CH2Cl2 / 1 h / 20 °C 3.1: 77 percent / NaBH4 / tetrahydrofuran; H2O / 16 h / 25 °C 4.1: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 5.1: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 6.1: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C 7.1: 78 percent / H2; HClO4 / Pd/C / ethanol / 48 h / 3040 Torr View Scheme

1: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 3: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C 4: 78 percent / H2; HClO4 / Pd/C / ethanol / 48 h / 3040 Torr View Scheme

1: 77 percent / NaBH4 / tetrahydrofuran; H2O / 16 h / 25 °C 2: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 3: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 4: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C 5: 78 percent / H2; HClO4 / Pd/C / ethanol / 48 h / 3040 Torr View Scheme

1: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 2: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C 3: 78 percent / H2; HClO4 / Pd/C / ethanol / 48 h / 3040 Torr View Scheme