sodium hydrogencarbonate in water; acetone

sodium hydroxide in methanol T=20°C; 1 h;

1: TFA / 2 h / 20 °C 2: aq. NaHCO3 / 6 h / 20 °C View Scheme

trifluoroacetic acid T=20°C; 2 h;

1: triethylamine; tetra-(n-butyl)ammonium iodide / acetone / |Reflux 2: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane 3: 4-(N,N-dimethlyamino)pyridine / acetonitrile / |Reflux 4: 5 palladium on charcoal; hydrogen / ethyl acetate / 760.05 Torr 5: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / toluene / 15 - 20 °C 6: acetic acid; zinc / methanol / 0.5 h / |Reflux 7: trifluoroacetic acid / dichloromethane / 20 °C 8: sodium hydrogencarbonate; dihydrogen peroxide / water; tetrahydrofuran / 20 °C View Scheme