Yield given. Multistep reaction;

1: 65 percent / NaH / dimethylformamide; CH2Cl2 / 3 h / -20 °C 2: 4-dimethylaminopyridine; Et3N / acetonitrile / 0.67 h / 20 °C 3: 1.1 g / isoamylnitrile / tetrahydrofuran / 2 h / Heating 4: 80 percent / methanolic ammonia / 4 h / 125 °C View Scheme

1: 65 percent / NaH / dimethylformamide; CH2Cl2 / 3 h / -20 °C 2: 65 percent / 1,4-diazabicyclo[2.2.2]octane / H2O / 0.75 h / 90 °C View Scheme

1: phenylmethanol 2: sodium nitrite; HBF4 / H2O 3: methanol 4: H2 / Pd/C View Scheme

1.1: dibutyltin(IV) oxide / methanol / 1 h / Heating 1.2: 85 percent / triethylamine / methanol / 12 h / 4 °C 2.1: 83 percent / lithium triethylborohydride / dimethylsulfoxide; tetrahydrofuran / 14 h / 35 °C 3.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 24 h / 45 °C 4.1: 60 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.5 h / 40 °C 5.1: 69 percent / hydrochloric acid / CH2Cl2; methanol / 1.5 h / 30 °C 6.1: 67 percent / 2-mercaptoethanol; NaOMe / methanol / 48 h / 50 °C View Scheme