1: 71 percent / tetrahydrofuran / 1 h / 0 °C 2: 91 percent / potassium hydroxide / aq. ethanol / 2.5 h / Ambient temperature 3: 60 percent / pyridine / Ambient temperature 4: thionyl chloride / diethyl ether / 4 h / Ambient temperature 5: 84 percent / pyridine / CH2Cl2 / 2 h / Heating 6: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 7: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 8: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 9: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1: thionyl chloride / diethyl ether / 4 h / Ambient temperature 2: 84 percent / pyridine / CH2Cl2 / 2 h / Heating 3: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 4: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 5: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 6: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 2: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 3: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 4: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1: 60 percent / pyridine / Ambient temperature 2: thionyl chloride / diethyl ether / 4 h / Ambient temperature 3: 84 percent / pyridine / CH2Cl2 / 2 h / Heating 4: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 5: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 6: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 7: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1: 91 percent / potassium hydroxide / aq. ethanol / 2.5 h / Ambient temperature 2: 60 percent / pyridine / Ambient temperature 3: thionyl chloride / diethyl ether / 4 h / Ambient temperature 4: 84 percent / pyridine / CH2Cl2 / 2 h / Heating 5: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 6: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 7: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 8: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1: 84 percent / pyridine / CH2Cl2 / 2 h / Heating 2: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 3: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 4: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 5: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 2: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 2: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 3: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

n-Bu2BOTf in toluene Heating;

hydrogen; palladium on activated charcoal