1: 79 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide 2: dimethylformamide / 145 °C 4: 70 percent / diisobutylaluminum hydride / diethyl ether 5: 1) tert-BuMgBr / 1) THF; 2) THF 6: 1) H2; 2) aq. HF / 1) Pd-C View Scheme

1: 70 percent / diisobutylaluminum hydride / diethyl ether 2: 1) tert-BuMgBr / 1) THF; 2) THF 3: 1) H2; 2) aq. HF / 1) Pd-C View Scheme

1: dimethylformamide / 145 °C 3: 70 percent / diisobutylaluminum hydride / diethyl ether 4: 1) tert-BuMgBr / 1) THF; 2) THF 5: 1) H2; 2) aq. HF / 1) Pd-C View Scheme

hydrogen fluoride; hydrogen; palladium on activated charcoal Yield given. Multistep reaction;

1: 1) tert-BuMgBr / 1) THF; 2) THF 2: 1) H2; 2) aq. HF / 1) Pd-C View Scheme