hydrogen; palladium on activated charcoal in tetrahydrofuran; methanol P=760 Torr;

carbon palladium in tetrahydrofuran; methanol

1: 64 percent / ethanol / 6 h 2: 93 percent / pyridine hydrochloride / 0.17 h / 150 °C 3: 75 percent / H2 / 5 percent Pd/C / methanol; tetrahydrofuran / 760 Torr View Scheme

1: zinc iodide / 2 h / Ambient temperature 2: lithium aluminum hydride / diethyl ether / 2 h 3: 64 percent / ethanol / 6 h 4: 93 percent / pyridine hydrochloride / 0.17 h / 150 °C 5: 75 percent / H2 / 5 percent Pd/C / methanol; tetrahydrofuran / 760 Torr View Scheme

1: 94 percent / methanol / Heating 2: 62 percent / diisobutylaluminum hydride / tetrahydrofuran / 4 h / 0 °C 3: zinc iodide / 2 h / Ambient temperature 4: lithium aluminum hydride / diethyl ether / 2 h 5: 64 percent / ethanol / 6 h 6: 93 percent / pyridine hydrochloride / 0.17 h / 150 °C 7: 75 percent / H2 / 5 percent Pd/C / methanol; tetrahydrofuran / 760 Torr View Scheme

1: 50 percent / sodium methoxide / ethanol; diethyl ether / Ambient temperature 2: 51 percent / aq. piperidinium acetate / H2O / 16 h / Heating 3: 61 percent / phosphorus pentachloride / 1 h / 120 °C 4: 94 percent / methanol / Heating 5: 62 percent / diisobutylaluminum hydride / tetrahydrofuran / 4 h / 0 °C 6: zinc iodide / 2 h / Ambient temperature 7: lithium aluminum hydride / diethyl ether / 2 h 8: 64 percent / ethanol / 6 h 9: 93 percent / pyridine hydrochloride / 0.17 h / 150 °C 10: 75 percent / H2 / 5 percent Pd/C / methanol; tetrahydrofuran / 760 Torr View Scheme

1: 51 percent / aq. piperidinium acetate / H2O / 16 h / Heating 2: 61 percent / phosphorus pentachloride / 1 h / 120 °C 3: 94 percent / methanol / Heating 4: 62 percent / diisobutylaluminum hydride / tetrahydrofuran / 4 h / 0 °C 5: zinc iodide / 2 h / Ambient temperature 6: lithium aluminum hydride / diethyl ether / 2 h 7: 64 percent / ethanol / 6 h 8: 93 percent / pyridine hydrochloride / 0.17 h / 150 °C 9: 75 percent / H2 / 5 percent Pd/C / methanol; tetrahydrofuran / 760 Torr View Scheme