hydrogenchloride in methanol T=45°C; 2 h;

trifluoroacetic anhydride in dichloromethane 6 h; Ambient temperature;

1: 1) tetramethylethylenediamine, sec-butyl lithium / 1) THF, pentane, -80 deg C, 20 min, 2) -80 deg C, 20 min 2: p-toluenesulfonic acid / toluene / 2 h / Ambient temperature 3: 96 percent / conc. H2SO4, H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 45 °C / 3750.3 Torr 4: 95 percent / CH2Cl2 / 6 h / Ambient temperature 5: 91 percent / conc. HCl / methanol / 2 h / 45 °C View Scheme

1: 96 percent / conc. H2SO4, H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 45 °C / 3750.3 Torr 2: 95 percent / CH2Cl2 / 6 h / Ambient temperature 3: 91 percent / conc. HCl / methanol / 2 h / 45 °C View Scheme

1: p-toluenesulfonic acid / toluene / 2 h / Ambient temperature 2: 96 percent / conc. H2SO4, H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 45 °C / 3750.3 Torr 3: 95 percent / CH2Cl2 / 6 h / Ambient temperature 4: 91 percent / conc. HCl / methanol / 2 h / 45 °C View Scheme