1: 1.) Et3OBF4; 2.) NaH / 1.) CH2Cl2, room temperature, 12 h; 2.) diglyme, 0 deg C 2: 95 percent / copper(I) iodide / tetrahydrofuran; various solvent(s) / 24 h / -20 - 0 °C View Scheme

1: 1.) Et3OBF4; 2.) NaH / 1.) CH2Cl2, room temperature, 12 h; 2.) diglyme, 0 deg C 2: 1.) H2; 2.) LiAlH4 / 1.) platinum 3: 99 percent / hydrogen bromide / 115 °C 4: 1.) cyanation; 2.) aklaline hydrolysis View Scheme

triethyloxonium tetra-fluoroborate; sodium hydride 1.) CH2Cl2, room temperature, 12 h; 2.) diglyme, 0 deg C; Yield given. Multistep reaction;