hydrogenchloride in ethyl acetate T=80°C; 1 h;

1: 1.) thionyl chloride / 1.) -10 deg C, 30 min, 2.) RT, 2 d 2: 69 percent / ethanol; H2O / 5 h / 80 °C 3: 74 percent / tetrahydrofuran / 1 h / 70 °C 4: 75 percent / 5 N NaOH / methanol / 1 h / 100 °C 5: 65 percent / diphenyl phosphorazidate (DPPA), NEt3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 20 deg C, 12 h 6: 82 percent / 1 N HCl / ethyl acetate / 1 h / 80 °C View Scheme

1: 74 percent / tetrahydrofuran / 1 h / 70 °C 2: 75 percent / 5 N NaOH / methanol / 1 h / 100 °C 3: 65 percent / diphenyl phosphorazidate (DPPA), NEt3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 20 deg C, 12 h 4: 82 percent / 1 N HCl / ethyl acetate / 1 h / 80 °C View Scheme

1: 65 percent / diphenyl phosphorazidate (DPPA), NEt3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 20 deg C, 12 h 2: 82 percent / 1 N HCl / ethyl acetate / 1 h / 80 °C View Scheme

1: 75 percent / 5 N NaOH / methanol / 1 h / 100 °C 2: 65 percent / diphenyl phosphorazidate (DPPA), NEt3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 20 deg C, 12 h 3: 82 percent / 1 N HCl / ethyl acetate / 1 h / 80 °C View Scheme

1: 69 percent / ethanol; H2O / 5 h / 80 °C 2: 74 percent / tetrahydrofuran / 1 h / 70 °C 3: 75 percent / 5 N NaOH / methanol / 1 h / 100 °C 4: 65 percent / diphenyl phosphorazidate (DPPA), NEt3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 20 deg C, 12 h 5: 82 percent / 1 N HCl / ethyl acetate / 1 h / 80 °C View Scheme