hydrogenchloride in methanol; water T=70°C; 1 h;

1: 93 percent / KOH / ethanol; H2O / 2 h / 25 °C 2: 95 percent / H2 / Pd/C / methanol / 2.5 h / 25 °C 3: 2.) Et3N, DMAP; 3.) MnO2 4: 54 percent / (NH4)2Ce(NO3)6 / acetonitrile; H2O / 0 °C 5: 41 percent / tetrahydrofuran / -78 - 25 °C View Scheme

1.1: 93 percent / KOH / ethanol; H2O / 2 h / 20 °C 2.1: 95 percent / H2 / Pd/C / methanol / 2.5 h / 20 °C / 800 - 900 Torr 3.1: acetonitrile / 48 h / 20 °C 3.2: Et3N; DMAP / CH2Cl2 / 4 h / 20 °C 3.3: 188 mg / Alox B Super 1; MnO2 / CH2Cl2 / 2 h / 20 °C 4.1: 95 percent / (NH4)2Ce(NO3)6 / acetonitrile; H2O / 2 h / 0 °C 5.1: 30 percent / tetrahydrofuran / 2.5 h / -78 °C View Scheme