Multi-step reaction with 12 steps
1: 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
2: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 12 h / Ambient temperature
3: pyridine / ) deg C, 1 h; RT, 5 h
4: 91 percent / NaI, NaHCO3 / acetone / 8 h
5: 10 0.6 m NaHMDS in toluene / 1) THF, 0 deg C, 30 min, 2) THF, toluene, HMPA, 0 deg C to RT
6: 99 percent / p-TsOH / methanol / 48 h
7: 82 percent / Et3N, DMAP / CH2Cl2 / 12 h
8: Et3N / -10 °C
9: 55percent aq. HF / acetonitrile / 3 h / 0 °C
10: NaH (60percent in oil) / tetrahydrofuran / 48 h
11: 1) 1.6 m nBuLi in hexane, 2) BF3*Et2O / 1) THF, -78 deg C, 30 min, 2) THF, hexane, 20 min, -78 deg C, 3) THF, hexane, ether, 1 h, -78 deg C
12: 99 percent / hydrogen / (triphenylphosphine)rhodium / benzene / 5 h
With
pyridine; dmap; n-butyllithium; boron trifluoride diethyl etherate; hydrogen fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide;
palladium on activated charcoal; (triphenylphosphine)rhodium;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; acetonitrile; benzene;