Multi-step reaction with 8 steps
1: 1. NaH / 1. THF, r.t., 90min, 2. 90min, r.t.
2: 85 percent / pyridine / 4-dimethylaminopyridine (DMAP) / 3 h / 0 °C
3: 1. Cs2CO3 / 1. DMF, 30min, 2. DMF, 10h, r.t.
4: 99 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 1 h / Ambient temperature
5: 74 percent / diethyl azodicarboxylate (DEAD), PPh3 / tetrahydrofuran / a.) 0 deg C, 1h, b.) r.t., 2h
6: 88 percent / MeONa / methanol / 0.08 h / Ambient temperature
7: 50 percent / DCC, 4-pyrrolidinopyridine (4-PP) / CH2Cl2 / 4 h / Ambient temperature
8: 92 percent / diphenylphosphorylazide (DPPA), triethylamine / dimethylformamide / 2 h / 0 °C
With
pyridine; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; caesium carbonate; 4-pyrrolidin-1-ylpyridine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate;
dmap;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)87908-4