hydrogenchloride in 1,4-dioxane T=20°C; Inert atmosphere;

in N,N-dimethyl-formamide T=24°C; 16 h; 0.2 M borate buffer, pH 8.0 (add. of 0.1 M NaOH);

1: 35 percent / NaBiO3 / ethyl acetate; acetic acid; H2O / 0.83 h 2: 15 percent / dimethylformamide / 16 h / 24 °C / 0.2 M borate buffer, pH 8.0 (add. of 0.1 M NaOH) View Scheme

1: hydrogenchloride / water / 24 h / 20 °C 2: sodium hydrogencarbonate / water; tetrahydrofuran / 24 h / 20 °C 3: N-iodo-succinimide / dichloromethane / 0.67 h / 0 °C 4: N-ethyl-N,N-diisopropylamine; pyridine; copper diacetate / dichloromethane / 48 h / 20 °C / |Molecular sieve 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C 6: lithium hydroxide hydrate / water; methanol / 1.5 h / 4 °C 7: hydrogenchloride / 1,4-dioxane / 20 °C / |Inert atmosphere View Scheme

1: sodium hydrogencarbonate / water; tetrahydrofuran / 24 h / 20 °C 2: N-iodo-succinimide / dichloromethane / 0.67 h / 0 °C 3: N-ethyl-N,N-diisopropylamine; pyridine; copper diacetate / dichloromethane / 48 h / 20 °C / |Molecular sieve 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C 5: lithium hydroxide hydrate / water; methanol / 1.5 h / 4 °C 6: hydrogenchloride / 1,4-dioxane / 20 °C / |Inert atmosphere View Scheme

1: N-iodo-succinimide / dichloromethane / 0.67 h / 0 °C 2: N-ethyl-N,N-diisopropylamine; pyridine; copper diacetate / dichloromethane / 48 h / 20 °C / |Molecular sieve 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C 4: lithium hydroxide hydrate / water; methanol / 1.5 h / 4 °C 5: hydrogenchloride / 1,4-dioxane / 20 °C / |Inert atmosphere View Scheme

1: N-ethyl-N,N-diisopropylamine; pyridine; copper diacetate / dichloromethane / 48 h / 20 °C / |Molecular sieve 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C 3: lithium hydroxide hydrate / water; methanol / 1.5 h / 4 °C 4: hydrogenchloride / 1,4-dioxane / 20 °C / |Inert atmosphere View Scheme

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C 2: lithium hydroxide hydrate / water; methanol / 1.5 h / 4 °C 3: hydrogenchloride / 1,4-dioxane / 20 °C / |Inert atmosphere View Scheme

1: lithium hydroxide hydrate / water; methanol / 1.5 h / 4 °C 2: hydrogenchloride / 1,4-dioxane / 20 °C / |Inert atmosphere View Scheme

hydrogen bromide