N-ethyl-N,N-diisopropylamine

1: (3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-aminium (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate With hydrogenchloride in ethyl acetate T=5°C; pH=1 - 2; 0.416667 h; 2: benzyl chloroformate With potassium carbonate in water; isobutyl methylketone T=20 - 30°C; 0.666667 h;

potassium carbonate in water; isobutyl methylketone

potassium carbonate in water; isobutyl methylketone

potassium carbonate in water; isobutyl methylketone

1: ethanol / 20 °C / Reflux; Resolution of racemate 2: potassium carbonate / water; isobutyl methylketone View Scheme

1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C View Scheme

1: pyridine / 24 h / 20 °C 2: sodium iodide / butanone / 24 h / 120 °C 3: zinc / ethanol / 1 h / 70 °C 4: sodium carbonate / ethanol / 1 h / 50 °C 5: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 6: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 7: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C View Scheme

1: perchloric acid / acetone / 24 h / Molecular sieve 2: pyridine / 24 h / 20 °C 3: sodium iodide / butanone / 24 h / 120 °C 4: zinc / ethanol / 1 h / 70 °C 5: sodium carbonate / ethanol / 1 h / 50 °C 6: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 7: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 8: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C View Scheme

1: sodium iodide / butanone / 24 h / 120 °C 2: zinc / ethanol / 1 h / 70 °C 3: sodium carbonate / ethanol / 1 h / 50 °C 4: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 5: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C View Scheme