hydrogen; palladium on activated charcoal in ethanol; dichloromethane P=15001.2 Torr; Yield given;

1: dicyclohexylcarbodiimide, N,N-dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: H2, Et3N / 10percent Pd/C / tetrahydrofuran / Ambient temperature View Scheme

1: NEt3 / CH2Cl2 / 2 h / Heating 2: H2 / 10percent Pd-C / CH2Cl2; ethanol / 15001.2 Torr View Scheme

1: dicyclohexylcarbodiimide, N,N-dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: H2, Et3N / 10percent Pd/C / tetrahydrofuran / Ambient temperature View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 4.5 h / 90 °C 2: potassium hydroxide / ethanol; water / 2 h / |Reflux 3: thionyl chloride / N,N-dimethyl-formamide / 0.5 h / 0 °C / |Reflux 4: triethylamine / butanone / 4.5 h / 0 °C / |Cooling with ice 5: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C View Scheme

1: potassium hydroxide / ethanol; water / 2 h / |Reflux 2: thionyl chloride / N,N-dimethyl-formamide / 0.5 h / 0 °C / |Reflux 3: triethylamine / butanone / 4.5 h / 0 °C / |Cooling with ice 4: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C View Scheme