sulfuric acid in tetrahydrofuran 18 h; Ambient temperature;

1: 95 percent / HCl / 0.01 h 2: 60 percent / cc. H2SO4 / tetrahydrofuran / 18 h / Ambient temperature View Scheme

hydrogenchloride; hydrogen; palladium 1.) ether, 20 deg C; 2.) methanol, acetic acid, 5 h, 20 deg C; Yield given. Multistep reaction;

1: 88 percent / diisopropyl ethylamine / 1.) 25 deg C, 0.5 h; 2.) reflux, 1.5 h 2: 69 percent / NaBH4, LiI / tetrahydrofuran / 22 h / 40 °C 3: 1.) DMSO, C2O2Cl2; 2.) N(C2H5)3 / 1.) CH2Cl2, -60 deg C, 15 min; 2.) -60 to 25 deg C 4: 80 percent / NaCH3COO / methanol / 1 h / Heating 5: 71 percent / NaBH3CN, 1 N HCl / methanol / 20 h / -40 °C 6: 2.) 10percent NH3 / 1.) CH3OH, 0 deg C, 3 h; 2.) CH3OH, 0.5 h 7: 84 percent / <(C6H5)3P>3RhCl / acetonitrile; H2O / 3 h / Heating 8: 76 percent / trifluoro acetic acid / 8 h / 0 °C 9: 46 percent / H2 / 10percent Pd/C / ethanol / 4 h 10: 1.) 6 N HCl; 2.) H2 / 2.) 10percent Pd/C / 1.) reflux, 2 h; 2.) H2O, 25 deg C, 7 h View Scheme