lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether T=0°C; 2 h;

1.1: bis(η3-allyl-μ-chloropalladium(II)); (R,R)-DACH phenyl Trost's ligand / tetrahydrofuran / 0.33 h / 40 °C / Inert atmosphere 1.2: 8 h / 40 °C / Inert atmosphere 1.3: 10 h / Inert atmosphere; Reflux 2.1: potassium hexamethylsilazane / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / toluene / 2 h / 0 °C / Inert atmosphere 3.2: 5 h / 60 °C / Inert atmosphere 3.3: 20 °C / Inert atmosphere; Molecular sieve 4.1: boron trifluoride diethyl etherate / 75 °C / Inert atmosphere 5.1: pyridine; 4-(N,N-dimethlyamino)pyridine / 1 h / 150 °C / Inert atmosphere; Microwave irradiation 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 7.1: hydrazine / ethanol / 10 h / 68 °C / Inert atmosphere View Scheme

1: 82 percent / sodium methoxide / 10 h / Ambient temperature 2: 77 percent / perchloric acid / ethyl acetate; H2O / 2 h / Ambient temperature 3: 70 percent / sodium methoxide / methanol / 7.5 h / Ambient temperature 4: 40 percent / sodium methoxide / benzene / 3 h / Heating 5: pyridine / 9 h / Ambient temperature 6: trimethylammonium acetate / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 3.5 h / Heating View Scheme

1: 82 percent / sodium methoxide / 10 h / Ambient temperature 2: 77 percent / perchloric acid / ethyl acetate; H2O / 2 h / Ambient temperature 3: 70 percent / sodium methoxide / methanol / 7.5 h / Ambient temperature 4: 40 percent / sodium methoxide / benzene / 3 h / Heating 5: pyridine / 9 h / Ambient temperature 6: trimethylammonium acetate / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 3.5 h / Heating View Scheme

1: 82 percent / sodium methoxide / 10 h / Ambient temperature 2: 77 percent / perchloric acid / ethyl acetate; H2O / 2 h / Ambient temperature 3: 70 percent / sodium methoxide / methanol / 7.5 h / Ambient temperature 4: 40 percent / sodium methoxide / benzene / 3 h / Heating 5: pyridine / 9 h / Ambient temperature 6: trimethylammonium acetate / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 3.5 h / Heating View Scheme