in tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide

lithium hydroxide in methanol; water T=6°C; 18 h;

1: 1.)conc. HCl, NaNO2, H2O, 2.) NaN3 / 1.) MeOAc, 0 deg C, 45 min, 2.) MeOAc, 0 deg C 15 min 2: 97 percent / LiOH*H2O / methanol; H2O / 18 h / 6 °C View Scheme

1: 1.) conc. H2SO4, 2.) N-iodosuccinimide / 1.) CH3CN, RT, 2.) CH3CN, RT, 2 h 2: 1.)conc. HCl, NaNO2, H2O, 2.) NaN3 / 1.) MeOAc, 0 deg C, 45 min, 2.) MeOAc, 0 deg C 15 min 3: 97 percent / LiOH*H2O / methanol; H2O / 18 h / 6 °C View Scheme