hydrogen; triethylamine; palladium on activated charcoal in tetrahydrofuran; ethanol P=760 Torr; 1 h;

1: 68 percent / H2 / Pd/C / methanol; tetrahydrofuran 2: 44 percent / diisopropylethylamine / acetonitrile / 20 h / Heating View Scheme

N-ethyl-N,N-diisopropylamine in acetonitrile 20 h; Heating;

in chloroform; acetonitrile

1: 300 mg / Na2S2O4 / methanol; H2O / Ambient temperature 2: 252 mg / CH2Cl2 / Ambient temperature 3: 258 mg / NaI / acetone / 4 h / Heating 4: i-Pr2NEt / acetonitrile / 80 °C 5: H2, Et3N / Pd/C / ethanol; tetrahydrofuran / 1 h / 760 Torr View Scheme

1: 252 mg / CH2Cl2 / Ambient temperature 2: 258 mg / NaI / acetone / 4 h / Heating 3: i-Pr2NEt / acetonitrile / 80 °C 4: H2, Et3N / Pd/C / ethanol; tetrahydrofuran / 1 h / 760 Torr View Scheme