1: NaOAc / ethanol / 4 h / Heating 2: 2N HCl / 20 h / Heating View Scheme

hydrogenchloride in methanol 2 h; Heating;

1: 90 percent / NaBH4 / ethanol / 1.5 h / 0 °C 2: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT 3: 27 percent / H2O / 5 h / 160 °C 4: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 5: 58 percent / piperidine / ethanol / 18 h / Heating 6: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 7: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme

1: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT 2: 27 percent / H2O / 5 h / 160 °C 3: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 4: 58 percent / piperidine / ethanol / 18 h / Heating 5: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 6: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme

1: 27 percent / H2O / 5 h / 160 °C 2: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 3: 58 percent / piperidine / ethanol / 18 h / Heating 4: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 5: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme

1: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 2: 58 percent / piperidine / ethanol / 18 h / Heating 3: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 4: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme

1: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 2: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone 3: NaOAc / ethanol / 4 h / Heating 4: 2N HCl / 20 h / Heating View Scheme

1: NaH / dimethylformamide; toluene / 2.5 h / 80 °C 2: 10percent aq. H2SO4 / 2 h / Heating 3: 90 percent / NaBH4 / ethanol / 1.5 h / 0 °C 4: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT 5: 27 percent / H2O / 5 h / 160 °C 6: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 7: 58 percent / piperidine / ethanol / 18 h / Heating 8: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 9: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme

1: 10percent aq. H2SO4 / 2 h / Heating 2: 90 percent / NaBH4 / ethanol / 1.5 h / 0 °C 3: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT 4: 27 percent / H2O / 5 h / 160 °C 5: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 6: 58 percent / piperidine / ethanol / 18 h / Heating 7: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 8: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme

1: 58 percent / piperidine / ethanol / 18 h / Heating 2: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 3: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme