tris-(dibenzylideneacetone)dipalladium(0); methanesulfonic acid; α,α'-bis(di-t-butylphosphino)-o-xylene T=90°C; P=22502.3 Torr; 20 h; AutoclaveInert atmosphereSchlenk technique;

sulfuric acid 2 h; Reflux;

1: oxalyl dichloride; N,N-dimethyl-formamide / hexane / 1.5 h / 20 °C / Inert atmosphere 2: 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 20 °C / Inert atmosphere 3: sodium cyanoborohydride / tetrahydrofuran; acetic acid / 2.08 h / 20 - 60 °C 4: hydrogenchloride; water / Reflux 5: sulfuric acid / 2 h / Reflux View Scheme

1: 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 20 °C / Inert atmosphere 2: sodium cyanoborohydride / tetrahydrofuran; acetic acid / 2.08 h / 20 - 60 °C 3: hydrogenchloride; water / Reflux 4: sulfuric acid / 2 h / Reflux View Scheme

1: sodium cyanoborohydride / tetrahydrofuran; acetic acid / 2.08 h / 20 - 60 °C 2: hydrogenchloride; water / Reflux 3: sulfuric acid / 2 h / Reflux View Scheme

1: hydrogenchloride; water / Reflux 2: sulfuric acid / 2 h / Reflux View Scheme

(i) (enzymatic oxidation), (ii) /BRN= 1098229/; Multistep reaction;

sulfuric acid; N-ethyl-aniline; sodium-lt;N-ethyl-anilinegt;

1: With Ba(OH)2 in tetrahydrofuran; methanol T=20°C; 18 h; 2: With hydrogenchloride in water