hydrogenchloride in water T=20°C; 10 h; Inert atmosphere; Overall yield = 76 percent; Overall yield = 9 mg;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in methanol; benzene 5 h; Heating;

hydrogenchloride 6 h; Ambient temperature;

1: 2.) aq. NH4Cl / 1.) THF, -78 deg C, 2.) from -78 deg C to 20 deg C 2: 1.) OsO4, K3Fe(CN)6, K2CO3, 2.) Na2SO3 / 1.) aq. t-BuOH, 20 deg C 3: 89 percent / H2 / Pd(OH)2/C / ethyl acetate / 20 °C / 4560 Torr 4: 1.) DIBAL-H, 2.) HCl/MeOH / 1.) CH2Cl2, -78 deg C View Scheme

1: 1.) OsO4, K3Fe(CN)6, K2CO3, 2.) Na2SO3 / 1.) aq. t-BuOH, 20 deg C 2: 89 percent / H2 / Pd(OH)2/C / ethyl acetate / 20 °C / 4560 Torr 3: 1.) DIBAL-H, 2.) HCl/MeOH / 1.) CH2Cl2, -78 deg C View Scheme

1: 89 percent / H2 / Pd(OH)2/C / ethyl acetate / 20 °C / 4560 Torr 2: 1.) DIBAL-H, 2.) HCl/MeOH / 1.) CH2Cl2, -78 deg C View Scheme

1: With diisobutylaluminium hydride in dichloromethane T=-78°C; Reduction; 2 h; 2: With hydrogenchloride in methanol Hydrolysis; 48 h;

1: 90 percent / triethylamine, (N,N-dimethylamino)pyridine / CH2Cl2 / 0.5 h / 0 °C 2: 80 percent / Amberlyst A 26 (CO32-) / benzene / 12 h / Heating 3: 1) NaH (50percent in mineral oil) / 1) THF a) 0 deg C b) 1h room temperature 2) 1.5h, 0 deg C 4: 95 percent / N-iodosuccinimide / CHCl3 / 8 h / Ambient temperature 5: 95 percent / 2N HCl / methanol / 24 h / Ambient temperature 6: 88 percent / tri-n-butyltin hydride, azobis(isobutyronitrile) / benzene; methanol / 5 h / Heating View Scheme

1: 80 percent / Amberlyst A 26 (CO32-) / benzene / 12 h / Heating 2: 1) NaH (50percent in mineral oil) / 1) THF a) 0 deg C b) 1h room temperature 2) 1.5h, 0 deg C 3: 95 percent / N-iodosuccinimide / CHCl3 / 8 h / Ambient temperature 4: 95 percent / 2N HCl / methanol / 24 h / Ambient temperature 5: 88 percent / tri-n-butyltin hydride, azobis(isobutyronitrile) / benzene; methanol / 5 h / Heating View Scheme

1: 56 percent / DIBALH / tetrahydrofuran; hexane / 1.5 h / -78 °C 2: 79 percent / HCl / 6 h / Ambient temperature View Scheme