Multi-step reaction with 10 steps
1: 85 percent / pyridine / 4-dimethylaminopyridine (DMAP) / 3 h / 0 °C
2: 1. Cs2CO3 / 1. DMF, 30min; 2. DMF, 10h, r.t.
3: 99 percent / H2 / 10percent Pd-C / methanol / 1 h
4: 84 percent / diethyl azodicarboxylate (DEAD), PPh3 / tetrahydrofuran / a.) 1h, 0 deg C, b.) 2h, r.t.
5: 85 percent / MeONa / methanol / 0.08 h / Ambient temperature
6: 50 percent / DCC, 4-pyrrolidinopyridine (4-PP) / CH2Cl2 / 4 h / Ambient temperature
7: 92 percent / diphenylphosphorylazide (DPPA), triethylamine / dimethylformamide / 2 h / 0 °C
8: trifluoroacetic acid (TFA) / CH2Cl2 / 1 h / 0 °C
9: triethylamine / benzene / 25 °C
10: 85 percent / diphenylphosphoryl azide (DPPA), triethylamine / dimethylformamide / 2 h / 0 °C
With
pyridine; diphenylphosphoranyl azide; hydrogen; sodium methylate; caesium carbonate; 4-pyrrolidin-1-ylpyridine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate;
dmap; palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)87908-4