palladium on activated charcoal in methanol P=760 Torr; Ambient temperature;

1: 1.) aluminum chloride / 1.) 1,2-dichloroethane, 20 min, 2.) 1,2-dichloroethane, 50 deg C, 1 h 2: dimethylformamide / 2 h / 60 °C 3: NaBH4 / ethanol / 1.) RT, 4.5 h, 2.) 50 deg C, 1 h 4: 94.5 percent / pyridine / Ambient temperature 5: 85.9 percent / 90percent nitric acid / acetic acid / 6 h / Ambient temperature 6: 93 percent / acetic acid, zinc dust / ethanol / 0.5 h / Ambient temperature 7: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF4, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h 8: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C 9: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 10: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 11: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: dimethylformamide / 2 h / 60 °C 2: NaBH4 / ethanol / 1.) RT, 4.5 h, 2.) 50 deg C, 1 h 3: 94.5 percent / pyridine / Ambient temperature 4: 85.9 percent / 90percent nitric acid / acetic acid / 6 h / Ambient temperature 5: 93 percent / acetic acid, zinc dust / ethanol / 0.5 h / Ambient temperature 6: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF4, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h 7: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C 8: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 9: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 10: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 2: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 3: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: 94.5 percent / pyridine / Ambient temperature 2: 85.9 percent / 90percent nitric acid / acetic acid / 6 h / Ambient temperature 3: 93 percent / acetic acid, zinc dust / ethanol / 0.5 h / Ambient temperature 4: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF4, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h 5: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C 6: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 7: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 8: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 2: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: NaBH4 / ethanol / 1.) RT, 4.5 h, 2.) 50 deg C, 1 h 2: 94.5 percent / pyridine / Ambient temperature 3: 85.9 percent / 90percent nitric acid / acetic acid / 6 h / Ambient temperature 4: 93 percent / acetic acid, zinc dust / ethanol / 0.5 h / Ambient temperature 5: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF4, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h 6: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C 7: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 8: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 9: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: 85.9 percent / 90percent nitric acid / acetic acid / 6 h / Ambient temperature 2: 93 percent / acetic acid, zinc dust / ethanol / 0.5 h / Ambient temperature 3: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF4, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h 4: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C 5: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 6: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 7: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF4, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h 2: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C 3: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 4: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 5: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme

1: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C 2: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C 3: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature 4: Pd/C / methanol / 760 Torr / Ambient temperature View Scheme