Multi-step reaction with 7 steps
1: 77 percent / diisobutylaluminum hydride / toluene / 1 h / -60 °C
2: 1.) K2CO3 / 1.) DMF, RT, 1.5 h, 2.) DMF, 95 deg C, 7 h
3: 79 percent / pyridinium p-toluenesulfonate / acetone; H2O / 15 h / Heating
4: 1.) n-BuLi / 1.) THF, 0 deg C, 90 min, 2.) THF, a) -78 deg C, 90 min, b) 0 deg C, 2 h
5: 100 percent / H2 / 10percent Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
6: 89 percent / 4.5 h / Ambient temperature
7: 94 percent / BH3 / tetrahydrofuran / 2 h / 0 °C
With
n-butyllithium; borane; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; water; acetone; toluene;
DOI:10.1021/ja953578v