Multi-step reaction with 9 steps
1: 98 percent / imidazole / dimethylformamide; tetrahydrofuran / 5 h / 20 °C
2: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / dioxane / 5 h / 20 °C
3: 94 percent / pyridine / 20 °C
4: 72 percent / sodium tert-butoxide; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / tris(dibenzylideneaceton)-dipalladium / toluene / 1 h / 100 °C
5: triethylamine; 4-(dimethylamino)pyridine / pyridine / 5 h / 20 °C
6: 78 percent / hydrochloric acid / methanol / 20 °C
7: 97 percent / pyridine / 20 °C
8: 79 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 20 °C
9: 88 percent / cyclohexene / Pd/C / ethanol / 3 h / Heating
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; acetic acid; triethylamine; triphenylphosphine; sodium t-butanolate; cyclohexene;
tris-(dibenzylideneacetone)dipalladium(0); palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; N,N-dimethyl-formamide; toluene;
4: Buchwald-Hartwig coupling;
DOI:10.1021/ol026474f