Dowex 50 x 2 (H(1+)) ion-exchange resin in ethanol 1 h; Ambient temperature;

1: 98 percent / tert-butylhydroperoxide / vanadyl acetylacetonate / benzene / 24 h / 40 °C 2: 82 percent / CrO3 / CH2Cl2 / 2 h / Ambient temperature 3: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to r.t., 6 h 4: 99 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 5: 91 percent / N,N-diisopropyloethylamine / CH2Cl2 / 12 h / Ambient temperature 6: 56 percent / CuSO4 / benzene / 12 h / Ambient temperature 7: 95 percent / Et3NHF / tetrahydrofuran / 3 h / Ambient temperature 8: 80 percent / lithium perhydro-9b-boraphenalyl hydride / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) room temp., 12 h 9: 1.) 47-52percent aq. HF, 2.) 5percent aq. HCl / 1.) acetonitrile, room temp., 30 min, 2.) THF, reflux, 20 h View Scheme

1: 1.) CuCN, / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -40 deg C to r.t., 7 h 2: 98 percent / tert-butylhydroperoxide / vanadyl acetylacetonate / benzene / 24 h / 40 °C 3: 82 percent / CrO3 / CH2Cl2 / 2 h / Ambient temperature 4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to r.t., 6 h 5: 99 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 6: 91 percent / N,N-diisopropyloethylamine / CH2Cl2 / 12 h / Ambient temperature 7: 56 percent / CuSO4 / benzene / 12 h / Ambient temperature 8: 95 percent / Et3NHF / tetrahydrofuran / 3 h / Ambient temperature 9: 80 percent / lithium perhydro-9b-boraphenalyl hydride / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) room temp., 12 h 10: 1.) 47-52percent aq. HF, 2.) 5percent aq. HCl / 1.) acetonitrile, room temp., 30 min, 2.) THF, reflux, 20 h View Scheme

sodium methylate in methanol 0.5 h; Ambient temperature;

1: 98 percent / pyridine / 18 h / Ambient temperature 2: 79 percent / bis(acetonitrile)palladium(II) chloride / tetrahydrofuran / 8 h / Ambient temperature 3: 68 percent / sodium methanolate / methanol / 0.5 h / Ambient temperature View Scheme

1: 79 percent / bis(acetonitrile)palladium(II) chloride / tetrahydrofuran / 8 h / Ambient temperature 2: 68 percent / sodium methanolate / methanol / 0.5 h / Ambient temperature View Scheme

1: 67.5 percent / H2, NaBH4/nickel acetate, 1,2-diaminoethane / ethanol / 1 h 2: 98 percent / pyridine / 18 h / Ambient temperature 3: 79 percent / bis(acetonitrile)palladium(II) chloride / tetrahydrofuran / 8 h / Ambient temperature 4: 68 percent / sodium methanolate / methanol / 0.5 h / Ambient temperature View Scheme

aluminum(i-butyl)2(2,6-di-tert-butyl-4-methylphenoxy) in toluene T=-70°C; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to r.t., 6 h 2: 99 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 3: 91 percent / N,N-diisopropyloethylamine / CH2Cl2 / 12 h / Ambient temperature 4: 56 percent / CuSO4 / benzene / 12 h / Ambient temperature 5: 95 percent / Et3NHF / tetrahydrofuran / 3 h / Ambient temperature 6: 80 percent / lithium perhydro-9b-boraphenalyl hydride / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) room temp., 12 h 7: 1.) 47-52percent aq. HF, 2.) 5percent aq. HCl / 1.) acetonitrile, room temp., 30 min, 2.) THF, reflux, 20 h View Scheme

1: 99 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 2: 91 percent / N,N-diisopropyloethylamine / CH2Cl2 / 12 h / Ambient temperature 3: 56 percent / CuSO4 / benzene / 12 h / Ambient temperature 4: 95 percent / Et3NHF / tetrahydrofuran / 3 h / Ambient temperature 5: 80 percent / lithium perhydro-9b-boraphenalyl hydride / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) room temp., 12 h 6: 1.) 47-52percent aq. HF, 2.) 5percent aq. HCl / 1.) acetonitrile, room temp., 30 min, 2.) THF, reflux, 20 h View Scheme