Multi-step reaction with 7 steps
1: 1) KHMDS / 1) THF, toluene, -78 deg C, 30 min, 2) THF, toluene, -78 deg C -> 0 deg C, 1 h; 0 deg C, 3 h
2: tetrahydrofuran; toluene / Ambient temperature
3: 86 percent / 30 percent H2O2 / ethyl acetate / 0.33 h / 0 °C
4: 40 percent / dimethylsulfoxide / 30 h / Ambient temperature
5: 1) BH3, 2) HCl / 1) THF, reflux, 1 h, 2) MeOH, reflux, 2 h
6: 81 percent / H2 / Pd-C / ethyl acetate / 10343 Torr
7: 63 percent / PDC / dimethylformamide / 48 h / Ambient temperature
With
hydrogenchloride; dipyridinium dichromate; borane; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane;
palladium on activated charcoal;
In
tetrahydrofuran; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9816109