hydrogen; palladium on activated charcoal in tetrahydrofuran; methanol P=1520 Torr;

hydrogen; palladium on activated charcoal in ethanol

hydrogen; palladium on activated charcoal in ethanol 4 h; Heating;

1: 1.) LHMDS / 1.) THF, room temperature, 50 min, 2.) toluene, 2 h. 2: 76 percent / NaBH4, HCl / tetrahydrofuran; ethanol / 2 h / 0 °C 3: 94 percent / AcOH / 5 h / 150 °C 4: 82 percent / H2 / Pd-C / tetrahydrofuran; methanol / 10 h / 760 Torr View Scheme

1: 76 percent / NaBH4, HCl / tetrahydrofuran; ethanol / 2 h / 0 °C 2: 94 percent / AcOH / 5 h / 150 °C 3: 82 percent / H2 / Pd-C / tetrahydrofuran; methanol / 10 h / 760 Torr View Scheme

2: 80 percent / H2 / 5percent Pd-C / ethanol / 1 h / Ambient temperature View Scheme

1: 94 percent / AcOH / 5 h / 150 °C 2: 82 percent / H2 / Pd-C / tetrahydrofuran; methanol / 10 h / 760 Torr View Scheme

1: diethyl phosphorocyanidate, triethylamine / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 40 min 3: 80 percent / H2 / 5percent Pd-C / ethanol / 1 h / Ambient temperature View Scheme

1: 95 percent / sulfur trioxide-pyridine complex, DMSO, Et3N / CH2Cl2 / 0.17 h / 10 - 20 °C 2: 61 percent / 0.4 M cerium chloride / methanol / 67 h / 40 - 45 °C 3: 10percent HCl / methanol / 1 h / Ambient temperature 4: diethyl phosphorocyanidate, triethylamine / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 40 min 6: 80 percent / H2 / 5percent Pd-C / ethanol / 1 h / Ambient temperature View Scheme

1: 61 percent / 0.4 M cerium chloride / methanol / 67 h / 40 - 45 °C 2: 10percent HCl / methanol / 1 h / Ambient temperature 3: diethyl phosphorocyanidate, triethylamine / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 40 min 5: 80 percent / H2 / 5percent Pd-C / ethanol / 1 h / Ambient temperature View Scheme