hydrogen; sodium hydrogencarbonate; palladium on activated charcoal in ethanol P=760 Torr; 2 h;

1: Mg / tetrahydrofuran / 20 h / Heating 2: CuI / tetrahydrofuran / 0.5 h / -3 °C 3: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 4: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 2: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: CuI / tetrahydrofuran / 0.5 h / -3 °C 2: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 3: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 2: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 3: Mg / tetrahydrofuran / 20 h / Heating 4: CuI / tetrahydrofuran / 0.5 h / -3 °C 5: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 6: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 2: Mg / tetrahydrofuran / 20 h / Heating 3: CuI / tetrahydrofuran / 0.5 h / -3 °C 4: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 5: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 57 percent / DMSO, NaOH / 4 h / 15 °C 2: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 3: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 4: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 5: Mg / tetrahydrofuran / 20 h / Heating 6: CuI / tetrahydrofuran / 0.5 h / -3 °C 7: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 8: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 1.) diisobutylaluminium hydride (DIBAL), 2.) aq. H2SO4 / 1.) THF, hexane, 25 deg C, 2 h, 2.) THF, hexane, 25 deg C, 2 h 2: 57 percent / DMSO, NaOH / 4 h / 15 °C 3: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 4: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 5: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 6: Mg / tetrahydrofuran / 20 h / Heating 7: CuI / tetrahydrofuran / 0.5 h / -3 °C 8: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 9: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C 6: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 7: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 57 percent / DMSO, NaOH / 4 h / 15 °C 2: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 3: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 4: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 5: Mg / tetrahydrofuran / 20 h / Heating 6: CuI / tetrahydrofuran / 0.5 h / -3 °C 7: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 8: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme