[Ru(η4-COD)(η3-methylallyl)2]; 2-(dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-imidazole; hydrogen in toluene T=160°C; P=37503.8 Torr; 24 h; AutoclaveInert atmosphere; regioselective reaction;

diisobutylaluminium hydride T=0 - 35°C; 4 h;

1: 69 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 2: 1.) Zn, PPh3 / 1.) CH2Cl2, RT, 72 h, 2.) CH2Cl2, RT, 96 h 3: 1.) MeLi / 1.) THF, Et2O, a) -78 deg C, 1 h, b) RT, 3 h, 2.) THF, Et2O, RT, 17 h 4: 1.) CuI / 1.) THF, Et2O, from -10 deg C to 0 deg C, 2.) THF, Et2O, -78 deg C, 7.5 h 5: LiAlH4 / diethyl ether / 6 h / Ambient temperature View Scheme

1: 84 percent / LiAlH4 / diethyl ether / 7 h / Heating 2: 69 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 3: 1.) Zn, PPh3 / 1.) CH2Cl2, RT, 72 h, 2.) CH2Cl2, RT, 96 h 4: 1.) MeLi / 1.) THF, Et2O, a) -78 deg C, 1 h, b) RT, 3 h, 2.) THF, Et2O, RT, 17 h 5: 1.) CuI / 1.) THF, Et2O, from -10 deg C to 0 deg C, 2.) THF, Et2O, -78 deg C, 7.5 h 6: LiAlH4 / diethyl ether / 6 h / Ambient temperature View Scheme

1: 1.) MeLi / 1.) THF, Et2O, a) -78 deg C, 1 h, b) RT, 3 h, 2.) THF, Et2O, RT, 17 h 2: 1.) CuI / 1.) THF, Et2O, from -10 deg C to 0 deg C, 2.) THF, Et2O, -78 deg C, 7.5 h 3: LiAlH4 / diethyl ether / 6 h / Ambient temperature View Scheme

1: 1.) CuI / 1.) THF, Et2O, from -10 deg C to 0 deg C, 2.) THF, Et2O, -78 deg C, 7.5 h 2: LiAlH4 / diethyl ether / 6 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether 6 h; Ambient temperature; Yields of byproduct given;