sodium tetrahydroborate in methanol 20 h; Ambient temperature;

ZnF2; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide T=80°C;

1: α,α-dimethyl-(4-bromophenyl)acetic acid methyl ester; ethynylmethyl carbinol With potassium carbonate; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) in toluene 24 h; Reflux; 2: With sulfuric acid; mercury(II) oxide in methanol; water T=25 - 35°C; 2 h; 3: 4-(hydroxy-diphenyl-methyl)-piperidine

1: 99 percent / LiAlH4 / diethyl ether 2: 97 percent / Et3N; 4-pyrrolidinopyridine / 0.33 h / 20 °C 3: 63.5 percent / AlCl3 / CS2 / 1.5 h / 0 - 5 °C 4: 68 percent / p-TsOH*H2O / benzene / 24 h / Heating 5: 99 percent / NaOH; MeOH / 0.5 h / 20 °C 6: 89 percent / Jones reagent / acetone / 0 °C 7: 92 percent / diethyl ether / 0 °C 8: 89 percent / HCl; H2O / tetrahydrofuran / 15 h / 20 °C 9: 95 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / 0 °C 10: 44 percent / K2CO3; KI / dimethylformamide; toluene / 7 h / Heating View Scheme

1: 97 percent / Et3N / tetrakis(triphenylphosphine)palladium(0), Cu2Br2 / 3.5 h / Heating 2: 100 percent / pyridine / CH2Cl2 / 20 h / Ambient temperature 3: 75 percent / K2CO3 / acetonitrile / 12 h / Heating 4: 75 percent / HgO, aq. H2SO4 / methanol / 3 h / 55 °C 5: 95 percent / NaBH4 / methanol / 20 h / Ambient temperature View Scheme

in toluene 3 h; Heating / reflux;

1.1: sulfuric acid / toluene / 16 h / 63 - 67 °C / Industry scale 2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / toluene / 24 h / Reflux 2.2: 2 h / 25 - 35 °C View Scheme

1.1: AlCl3, aluminium chloride / Industry scale 2.1: sodium hydrogencarbonate; bromine / water / 13 h / 25 - 35 °C / Industry scale 2.2: 0 - 10 °C / pH 5 3.1: sulfuric acid / toluene / 16 h / 63 - 67 °C / Industry scale 4.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / toluene / 24 h / Reflux 4.2: 2 h / 25 - 35 °C View Scheme

potassium carbonate; potassium iodide in N,N-dimethyl-formamide; toluene Substitution; 7 h; Heating;

1: 100 percent / pyridine / CH2Cl2 / 20 h / Ambient temperature 2: 75 percent / K2CO3 / acetonitrile / 12 h / Heating 3: 75 percent / HgO, aq. H2SO4 / methanol / 3 h / 55 °C 4: 95 percent / NaBH4 / methanol / 20 h / Ambient temperature View Scheme