1: 77 percent / pyridine / 0.75 h / 20 °C 2: 12.6 mg / LiBH(Et)3 / tetrahydrofuran / 0.25 h / 20 °C 3: 73 percent / NaH / dimethylformamide / 13 h / 90 °C 4: 2.6 mg / hydrogen / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 51 percent / pyridine / 3.5 h / -25 - -5 °C 2: 30 percent / LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3: 77 percent / pyridine / 0.75 h / 20 °C 4: 12.6 mg / LiBH(Et)3 / tetrahydrofuran / 0.25 h / 20 °C 5: 73 percent / NaH / dimethylformamide / 13 h / 90 °C 6: 2.6 mg / hydrogen / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 30 percent / LiAlH4 / tetrahydrofuran / 2 h / 20 °C 2: 77 percent / pyridine / 0.75 h / 20 °C 3: 12.6 mg / LiBH(Et)3 / tetrahydrofuran / 0.25 h / 20 °C 4: 73 percent / NaH / dimethylformamide / 13 h / 90 °C 5: 2.6 mg / hydrogen / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 240 mg / H2 / 10 percent palladium on charcoal / ethyl acetate / 0.75 h 2: 3.3 g / toluene-p-sulphonic acid / benzene / 1 h / Heating 3: 900 mg / carbon tetrachloride, pyridine, triphenylphosphine / 3 h / Heating 4: 650 mg / tributyltin hydride, 2,2-azobisisobutyronitrile / benzene / 3 h / Heating 5: concd. sulphuric acid / ethanol; H2O / 0.17 h / Heating 6: 1.) sodium hydride/dimethyl sulphoxide / 1.) rt., 1 h; 2.) THF, rt., 3 h: 60 deg C, 1 h 7: lithium aluminium hydride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 290 mg / 10 percent sodium hydroxide / methanol / 0.08 h / Heating 2: 240 mg / H2 / 10 percent palladium on charcoal / ethyl acetate / 0.75 h 3: 3.3 g / toluene-p-sulphonic acid / benzene / 1 h / Heating 4: 900 mg / carbon tetrachloride, pyridine, triphenylphosphine / 3 h / Heating 5: 650 mg / tributyltin hydride, 2,2-azobisisobutyronitrile / benzene / 3 h / Heating 6: concd. sulphuric acid / ethanol; H2O / 0.17 h / Heating 7: 1.) sodium hydride/dimethyl sulphoxide / 1.) rt., 1 h; 2.) THF, rt., 3 h: 60 deg C, 1 h 8: lithium aluminium hydride / tetrahydrofuran / 1 h / Ambient temperature View Scheme