Multi-step reaction with 12 steps
1: 2,6-dimethylpyridine / dichloromethane / 0.75 h / 20 °C
2: diisobutylaluminium hydride / dichloromethane / 2 h / -40 - -10 °C
3: triethylamine / dichloromethane / 0 - 20 °C
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 20 °C
5: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / dichloromethane / 7 h / 0 - 20 °C
6: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C
7: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C
8: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 1 h
9: 1-ethyl-piperidine; HATU / acetonitrile / 12 h / 0 - 20 °C
10: water; lithium hydroxide / tert-butyl alcohol
11: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
12: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; N,N-dimethyl-formamide / 72 h / 0 - 20 °C
With
1-ethyl-piperidine; 2,6-dimethylpyridine; dmap; sodium chlorite; 1-hydroxy-7-aza-benzotriazole; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; lithium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2011.08.158