ammonium hydroxide in methanol T=85°C; 24 h;

1: 1.) KOH / 1) 1,4-dioxane, reflux, 1 h; 2) 1,4-dioxane, reflux, overnight 2: Et3N / acetone / 0.17 h / -30 °C 3: NaN3 / H2O / 0.5 h / Ambient temperature 4: toluene / Heating 5: 95 percent / KOH / tetrahydrofuran; H2O / 0 °C 6: 98 percent / Et3N / CH2Cl2 / 0 °C 7: 1.) N2O4, 2.) NaOAc / 1) CCl4, 0-5 deg C, 5 min; 2) CCl4, 0-5 deg C, 30 min 8: 86 percent / petroleum ether / Heating 9: Na, NH3 / dioxane / 0.17 h / -70 °C 10: 70 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 11: 1.) Et3N, 2.) bis(dibenzylideneacetone)palladium(0), triisopropyl phosphite / 1) THF, hexane, 60 deg C, 10-20 min; 2) THF, hexane, 60 deg C, 1-2 h; further reagent and solvent 12: 97 percent / Na, methanol / Ambient temperature View Scheme

1: 70 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 2: 1.) Et3N, 2.) bis(dibenzylideneacetone)palladium(0), triisopropyl phosphite / 1) THF, hexane, 60 deg C, 10-20 min; 2) THF, hexane, 60 deg C, 1-2 h; further reagent and solvent 3: 97 percent / Na, methanol / Ambient temperature View Scheme

1: 96 percent / benzene / 5 h / 50 °C 2: 91 percent / sodium borohydride / methanol / 1 h / Ambient temperature 3: 93 percent / 25 percent ammonia / methanol / 24 h / 85 °C View Scheme

1: 91 percent / sodium borohydride / methanol / 1 h / Ambient temperature 2: 93 percent / 25 percent ammonia / methanol / 24 h / 85 °C View Scheme

1: 81 percent / DAST / CH2Cl2 / 0.5 h / -78 °C 2: 1.) LiCl, 2.) aq. AcOH / 1.) DMF, 100 deg C, 8 d, 2.) reflux, 0.5 h View Scheme

1: 1.) Et3N, 2.) bis(dibenzylideneacetone)palladium(0), triisopropyl phosphite / 1) THF, hexane, 60 deg C, 10-20 min; 2) THF, hexane, 60 deg C, 1-2 h; further reagent and solvent 2: 97 percent / Na, methanol / Ambient temperature View Scheme

1: 98 percent / imidazole / dimethylformamide / 15 h / Ambient temperature View Scheme