1: 92 percent / aq. HCl / 4 h / Heating 2: 88 percent View Scheme

hydrogenchloride Decarboxylation; 4 h; Heating;

sodium; xylene

1: N-(ethoxycarbonyl)-α-amino methyl carboxylic ester With sodium hydride in benzene T=20 - 100°C; Metallation; 12 h; 2: ethyl acrylate in benzene Cyclization; 2 h; Heating;

sodium hydride; oil in toluene 3 h; Heating;

toluene

sodium; benzene anschliessendes Behandeln mit Acrylsaeure-aethylester;

1: tert-butyl alcohol / 12 h / 85 °C 2: trichlorophosphate / acetonitrile / Reflux 3: trimethylsilyl iodide / acetonitrile / 4 h / 81 °C 4: N-ethyl-N,N-diisopropylamine / 1,4-dioxane; water / 20 - 45 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.67 h / 120 °C / Inert atmosphere; Microwave irradiation 6: potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 7: hydrogenchloride / 1,4-dioxane; methanol / 12 h / 23 °C 8: triethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 75 °C View Scheme

N,N'-dimethyl-N,N'-propyleneurea; lithium diisopropyl amide 1.) THF, -78 deg C; Yield given. Multistep reaction;