1: 93 percent / 6 h / 110 °C 2: 90 percent / nickel boride, hydrazine hydrate / ethanol / Heating View Scheme

T=120°C; P=10 - 20 Torr; 2.5 h;

pyrrolidine; hydrazine hydrate; nickel 1.) DMF, 125 deg C, 3 h; 2.) methanol, 50-60 deg C, 3 h; Yield given. Multistep reaction;

1: dimethylformamide / 30 h / Heating 2: 83.6 percent / Silica gel (100-200 mesh) / CH2Cl2; H2O / 4 h / Ambient temperature 3: 67.7 percent / H2 / 10percent Pd/C, PtO2*2H2O / methanol / 15 h / 60 °C / 52956.6 Torr View Scheme

1: With acetic acid; zinc in methanol T=0°C; 1 h; 2: With sodium hydrogencarbonate in water; ethyl acetate

1.1: hydrogen; 3 platinum on carbon / ethanol / 21.5 h / 258.58 - 2585.81 Torr 2.1: potassium acetate; acetic anhydride / toluene / 3.5 h 2.2: 18 h / 80 °C 2.3: 4 h / 40 °C 3.1: caesium carbonate / N,N-dimethyl-formamide / 5.25 h / 40 - 90 °C 4.1: hydrogen; palladium(II) oxide hydrate / tert-butyl methyl ether / 12 h / 2430.66 Torr / |Inert atmosphere 5.1: tert-butyl methyl ether / 760.05 Torr / |Heating; |Inert atmosphere 5.2: 36 h / 65 °C / |Heating; |Inert atmosphere 6.1: potassium hydroxide / tetrahydrofuran; water / 3 h View Scheme

1: 1.) pyrrolidine; 2.) 85percent N2H4 / 2.) Raney Ni / 1.) DMF, 125 deg C, 3 h; 2.) methanol, 50-60 deg C, 3 h 2: 76 percent / trifluoroacetic acid / 0.5 h / Ambient temperature 3: 74 percent / 1.) LiAlH4; 2.) HCl / tetrahydrofuran / 0.25 h / Heating 4: 34 percent / H2O / 1 h / Heating 5: 51 percent / H2 / 10percent Pd/C / ethanol / 1 h / 775.7 Torr / Ambient temperature View Scheme

diethyl ether; potassium ethanolate; toluene Behandeln des Reaktionsprodukts in wss. NaOH mit Na2S2O4;