1: 1.) 2.3M t-butyllithium / 1) THF, pentane, -78 deg C, 30 min, 2) THF, pentane, -100 deg C, 30 min. 2: hidrazine / aq. ethanol; acetic acid / 50 °C View Scheme

Yield given. Multistep reaction;

1: 1) sec-BuLi / 1) THF, cyclohexane, -78 deg C, 1 h, 2) -100 deg C, 5 h 2: hydrazine, acetic acid / ethanol; H2O / 50 °C 3: 2) NaBH4 / 1) methanol, H2O, rt, 0.5 h, 2) 1 h View Scheme