Multi-step reaction with 10 steps
1: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, reflux, 45 min, 2.) r.t., 1.5 h
2: 57 percent / Jones reagent, MgSO4 / acetone / 0.17 h / 0 - 5 °C
3: 86 percent / hydrogen / 5 percent Pd/C / ethyl acetate / 1 h / Ambient temperature
4: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 15 min
5: 3.28 g / pyridine / 1 h / Ambient temperature
6: 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 0.17 h / Ambient temperature
7: 1.) CuI / 1.) Et2O, 0 deg C, 2.) 0-5 deg C, 15 min
8: lithium bis(trimethylsilyl)amide / 0.08 h / -78 °C
9: 100 percent / 4 N aq. HCl / methanol / 0.33 h / Heating
10: 1.) triphenyl phosphine, diethyl azodicarboxylate, 2.) diphenylphosphoryl azide / 1.) THF, r.t., 5 min, 2.) r.t., 1 h
With
pyridine; hydrogenchloride; copper(l) iodide; jones reagent; DBN; diphenylphosphoranyl azide; hydrogen; magnesium sulfate; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethyl acetate; acetone;
DOI:10.1016/S0040-4020(01)87085-X