Multi-step reaction with 12 steps
1.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 - 20 °C
2.1: 2,6-dimethylpyridine / dichloromethane
3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water
4.1: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / toluene / 75 °C
5.1: 75 °C
6.1: Wilkinson's catalyst / ethanol; water / Reflux
6.2: 20 °C / pH 10 / aq. buffer
7.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C
8.1: methanol; potassium carbonate / 20 °C
9.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C
10.1: palladium on activated charcoal; hydrogen / methanol
11.1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide
12.1: hydrogenchloride / 1,4-dioxane; water
With
4-methyl-morpholine; 2,6-dimethylpyridine; hydrogenchloride; methanol; Wilkinson's catalyst; di-n-butylboryl trifluoromethanesulfonate; diphenyl phosphoryl azide; palladium on activated charcoal; HATU; hydrogen; dihydrogen peroxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
4.1: Curtius rearrangement / 7.1: Mitsunobu reaction / 9.1: Mitsunobu reaction;
DOI:10.1016/j.bmcl.2011.06.109