Multi-step reaction with 7 steps
1: pyridine / 0 deg C, 1 h; RT, 5 h
2: NaI, NaHCO3 / acetone / 6 h
3: 1) 1.56 M nBuLi in hexane / 1) THF, -40 deg C then 0 deg C, 40 min, 2) THF, HMPA, 0 deg C, 1 h then 1 h, RT
4: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 12 h / Ambient temperature
5: pyridine / ) deg C, 1 h; RT, 5 h
6: 91 percent / NaI, NaHCO3 / acetone / 8 h
7: 10 0.6 m NaHMDS in toluene / 1) THF, 0 deg C, 30 min, 2) THF, toluene, HMPA, 0 deg C to RT
With
pyridine; n-butyllithium; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; sodium iodide;
palladium on activated charcoal;
In
ethyl acetate; acetone;