hydrogen; palladium on activated charcoal in methanol T=20°C; P=760 Torr; 15 h;

1: 76 percent / NH4H2PO2; triethylborane / methanol; hexane / 2 h / 20 °C 2: 71 percent / ethyldiisopropylamine; trimethylsilyl chloride / CH2Cl2 / 12 h / cooling 3: 96 percent / H2 / Pd/C / methanol / 15 h / 20 °C / 760 Torr View Scheme

1: 71 percent / ethyldiisopropylamine; trimethylsilyl chloride / CH2Cl2 / 12 h / cooling 2: 96 percent / H2 / Pd/C / methanol / 15 h / 20 °C / 760 Torr View Scheme

1: 95 percent / NaHCO3; tricaprylmethylammonium chloride / H2O; CH2Cl2 / 72 h 2: 76 percent / NH4H2PO2; triethylborane / methanol; hexane / 2 h / 20 °C 3: 71 percent / ethyldiisopropylamine; trimethylsilyl chloride / CH2Cl2 / 12 h / cooling 4: 96 percent / H2 / Pd/C / methanol / 15 h / 20 °C / 760 Torr View Scheme