hydrogen; palladium dihydroxide in ethyl acetate P=2068.65 Torr; 24 h;

1: p-toluenesulfonic acid / toluene / Heating 2: NaBH4 / methanol / Ambient temperature 3: 99 percent / tetrahydrofuran / 48 h / Ambient temperature 4: 45 percent / H2 / 10percent Pd/C / ethanol / 18 h / 2585.7 - 3102.9 Torr 5: 0.75 g / K2CO3, KI / acetonitrile / 18 h / Heating View Scheme

1: 5 N HCl, sodium cyanoborohydride, 3 A molecular sieves / methanol / 72 h / Ambient temperature 2: 3.5 g / 4 h / Heating 3: 76 percent / conc. HCl, 10percent Pd/C, H2 / ethanol / 21 h / 35 °C / 2585.7 Torr View Scheme

1.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate / 20 °C / 2250.23 Torr 2.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethylene glycol dimethyl ether / 0.33 h / 80 °C / |Microwave irradiation; |Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C View Scheme

sodium t-butanolate in tetrahydrofuran T=0 - 20°C;

lithium hexamethyldisilazane in tetrahydrofuran T=-78 - 25°C; 2.5 h;

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 1 h;

1: 2.) NaBH4 / 1.) toluene, EtOH, 2.) toluene, EtOH 2: HCl, H2 / Pd(OH)2/C / methanol / 120 h / 2068.6 Torr View Scheme