1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / -35 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C 3: hydrogen; 2,6-dimethylpyridine / palladium 10 on activated carbon / water; tetrahydrofuran / 20 - 25 °C / 13501.4 Torr View Scheme

N-ethyl-N,N-diisopropylamine in ethyl acetate T=-15 - -10°C; 5 h;

1: 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate With N-ethyl-N,N-diisopropylamine; phosphorochloridic acid diphenyl ester in acetonitrile T=10 - 15°C; 5 h; 2: (2S,4S)-2-dimethylaminocarbonyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine With N-ethyl-N,N-diisopropylamine in acetonitrile T=10 - 15°C; 5 - 8 h;

1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / -35 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C View Scheme

1: diisopropylethylamine / acetonitrile / 0.5 h / -10 °C 2: diisopropylethylamine / acetonitrile / 0.67 h / -5 °C 3: H2 / 10percent Pd / C / tetrahydrofuran; H2O / 1.67 h / 3040 Torr / Ambient temperature 4: ethyl formimidate hydrochloride, 1N NaOH / tetrahydrofuran; H2O / 0.08 h / 0 °C View Scheme

1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / -35 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C 3: hydrogen; MgCl2*6H2O / water; tetrahydrofuran / 25 - 35 °C / 3750.38 Torr View Scheme

Multi-step reaction with 4 steps 1: 1,1'-carbonyldiimidazole / acetonitrile2: hydrogenchloride; water / ethyl acetate3: triethylamine / ethyl acetate; toluene4: dirhodium(II) tetraoctanoate / acetone / Reflux  

Multi-step reaction with 4 steps 1: 1,1'-carbonyldiimidazole / acetonitrile2: hydrogenchloride; water / ethyl acetate3: triethylamine / ethyl acetate; toluene4: dirhodium(II) tetraoctanoate / acetone / Reflux  

Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / -35 °C2: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C  

Multi-step reaction with 2 steps 1: diisopropylethylamine / acetonitrile / 0.5 h / -10 °C2: diisopropylethylamine / acetonitrile / 0.67 h / -5 °C