hydrogenchloride; triethanolamine; magnesium sulfate in n-heptane; water

4-(N,N-dimethlyamino)pyridine; (R)-N-(tert-butoxycarbonyl)proline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in 1,2-dichloro-ethane T=0 - 20°C;

4-(N,N-dimethlyamino)pyridine; 1-(tert-butoxycarbonyl)-L-proline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in 1,2-dichloro-ethane T=0 - 20°C;

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 2: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 3: N-bromosuccinmide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere 4: 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere 5: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene] dichloromethane; potassium acetate / dimethyl sulfoxide / 12 h / 80 °C / Inert atmosphere 6: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 12 h / 40 °C / Inert atmosphere 7: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / ethylene glycol dimethyl ether; water / 16 h / 87 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; methanol; water / 1 h / Inert atmosphere View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; (R)-N-(tert-butoxycarbonyl)proline / 1,2-dichloro-ethane / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 2.2: Reflux 3.1: 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 20 °C 4.1: sodium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / N,N-dimethyl-formamide / 90 °C 5.1: water; lithium hydroxide hydrate / tetrahydrofuran / 20 °C 5.2: pH 5 6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C 6.2: 0.5 h / 20 °C 7.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 2: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 3: N-bromosuccinmide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere View Scheme

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 2: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux View Scheme

di-isopropyl azodicarboxylate; triphenylphosphine in tetrahydrofuran T=0 - 20°C; 4 h; Inert atmosphere;