hydrogen; palladium dihydroxide in tetrahydrofuran P=3800 Torr; 25 h;

triethylamine in methanol; dichloromethane; water; N,N-dimethyl-formamide

1: 32 percent / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h, 3.) 4 deg C, overnight 3: 91 percent / AIBN, Bu3SnH / xylene / 1 h / Heating 4: 95 percent / H2 / Pd(OH)2/C / tetrahydrofuran / 25 h / 3800 Torr View Scheme

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h, 3.) 4 deg C, overnight 2: 91 percent / AIBN, Bu3SnH / xylene / 1 h / Heating 3: 95 percent / H2 / Pd(OH)2/C / tetrahydrofuran / 25 h / 3800 Torr View Scheme

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h, 3.) 4 deg C, overnight 2: 81 percent / AIBN, Bu3SnH / toluene / Heating 3: 95 percent / H2 / Pd(OH)2/C / tetrahydrofuran / 25 h / 3800 Torr View Scheme

1: 91 percent / AIBN, Bu3SnH / xylene / 1 h / Heating 2: 95 percent / H2 / Pd(OH)2/C / tetrahydrofuran / 25 h / 3800 Torr View Scheme

1: 81 percent / AIBN, Bu3SnH / toluene / Heating 2: 95 percent / H2 / Pd(OH)2/C / tetrahydrofuran / 25 h / 3800 Torr View Scheme

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