1.1: palladium diacetate; p-benozquinone / dimethyl sulfoxide / 48 h / 40 °C / |Molecular sieve 2.1: sodium hydroxide / water; methanol / 0.5 h / 20 °C 3.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 4 h / 100 °C 5.1: water; AD-mix-β / tert-butyl alcohol / 12 h / 0 °C 6.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere 7.1: hydrogen; 10 Pd/C / methanol / 24 h / 20 °C / 2068.65 Torr 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere 9.1: hydrogenchloride; methanol / water / 6 h / 20 °C 10.1: sodium periodate / water; methanol / 1 h / 0 °C 11.1: sodium tetrahydroborate / water; methanol / 0.5 h / 20 °C 11.2: 3 h / |Reflux 12.1: ammonia / water; methanol / 20 °C View Scheme