1: HBr, acetic acid / 1 h / Ambient temperature 2: H2, thriethylamine / Pd/C / ethyl acetate / 76000 Torr / Ambient temperature 3: aq. perchloric acid / 1 h 4: H2, triethylamine / Pd/C / ethyl acetate / 20 h / 76000 Torr / Ambient temperature 5: 1.) KOH, 2.) 2M HCl / 2.) 50 deg C View Scheme

1: HBr, acetic acid / 1 h / Ambient temperature 2: H2, thriethylamine / Pd/C / ethyl acetate / 76000 Torr / Ambient temperature 3: aq. perchloric acid / 1 h 4: H2, triethylamine / Pd/C / ethyl acetate / 20 h / 76000 Torr / Ambient temperature 5: 1.) KOH, 2.) 2M HCl / 2.) 50 deg C 6: 83 percent / pyridine / 0 °C View Scheme

potassium hydroxide in isopropyl alcohol

hydrogenchloride; methanesulfonic acid in water; acetone T=20°C; 20 h;

hydrogenchloride; methanesulfonic acid in water T=20°C; 73 h;

1: aq. HCl 2: MeSO3H / acetone / 20 h / 20 °C 3: aq. AcOH / 16.5 h / 28 - 29 °C View Scheme