1: aq. HBr / 8 h / Heating 2: H2; H2SO4 / PtO2 / methanol / 18 h / 20 °C 3: HNO3; AcOH / 2 h / 20 °C 4: Et3N; H2O / tetrahydrofuran / 18 h / 20 °C 5: K2CO3 / acetone / 18 h / Heating 6: H2 / Pd/C / 18 h / 50 °C / 2250.18 Torr View Scheme

1: hydrogen bromide / water 2: hydrogen; platinum(IV) oxide; sulfuric acid / methanol 3: acetic acid; nitric acid 4: triethylamine / tetrahydrofuran; water 5: potassium carbonate / acetone / |Heating 6: hydrogen; palladium on activated charcoal 7: hydrogenchloride / diethyl ether; isopropyl alcohol / |Heating View Scheme

1: aq. HBr / 8 h / Heating 2: H2; H2SO4 / PtO2 / methanol / 18 h / 20 °C View Scheme

1: aq. HBr / 8 h / Heating 2: H2; H2SO4 / PtO2 / methanol / 18 h / 20 °C 3: HNO3; AcOH / 2 h / 20 °C 4: Et3N; H2O / tetrahydrofuran / 18 h / 20 °C 5: K2CO3 / acetone / 18 h / Heating 6: H2 / Pd/C / 18 h / 50 °C / 2250.18 Torr 7: HCl / diethyl ether; propan-2-ol / 18 h / Heating 8: i-Pr2NEt / propan-2-ol / 48 h / Heating View Scheme