sodium periodate; sodium hydrogencarbonate 1.) ethanol, RT, 2 h, 2.) ethanol, 0 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction;

1: 95 percent / H2 / 10percent Pd-C / ethanol / 10 h / Ambient temperature 2: 88 percent / trifluoroacetic acid / tetrahydrofuran; H2O / 3 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 1.) RT, overnight, 2.) reflux, 6 h;

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 1.2: 4 h / 110 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 2 h / 0 °C / Inert atmosphere 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: water; acetic acid / 2 h / 20 - 50 °C 5.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 6.1: pyridine; hydrogen fluoride / tetrahydrofuran / 7 h / 0 - 20 °C / Inert atmosphere 7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 7.2: -78 - 20 °C / Inert atmosphere 8.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere 8.2: 0.67 h / 0 °C / Inert atmosphere 8.3: 3.5 h / 0 - 20 °C / Inert atmosphere 9.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere 10.1: n-butyllithium; chloro-trimethyl-silane; triethylamine; diisopropylamine / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere 10.2: 120 °C / Inert atmosphere 11.1: methanol; diethyl ether; benzene / 1.5 h / 6 - 20 °C / Inert atmosphere 12.1: pyridine; hydrogen fluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 13.1: pyridinium chlorochromate / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere; Celite 14.1: toluene / 110 °C / Inert atmosphere; Molecular sieve; Sealed tube 14.2: 5.58 h / 0 - 20 °C / Molecular sieve 15.1: PHT / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere 15.2: 12 h / 20 °C / Inert atmosphere 16.1: sodium tetrahydroborate / isopropyl alcohol / 77 h / 20 - 50 °C / Inert atmosphere View Scheme

sulfuric acid in methanol 0.5 h; Ambient temperature;

sulfuric acid in methanol 0.5 h; Ambient temperature;

1: 99 percent / H2 / PtO2 / ethyl acetate / 4 h / 20 °C 2: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 20 °C View Scheme

hydrogenchloride in ethanol; water T=20°C; 2.5 h; Inert atmosphere;

hydrogen; PtO2 in ethyl acetate