Multi-step reaction with 11 steps
1: 103.1 g / HCl / ethanol / 16 h / Ambient temperature
2: 53 percent / methanol / 72 h / 5 °C
3: 73 percent / methanol / 1.5 h / 100 °C
4: 89 percent / pyridine, lithium iodide / 2 h / Heating
5: 1.) Et3N, diphenyl phosphorazidate / 1.) 100 deg C, 2 h, 2.) 100 deg C, 12 h
6: 1N aq. HCl / tetrahydrofuran / 8 h / Heating
7: sodium chlorite, sodium dihydrogen phosphate monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature
8: 1-hydroxybenzotriazole hydrate, Et3N, EDC / dimethylformamide / 16 h
9: anisole, trifluoromethanesulfonic acid / CH2Cl2 / 0.25 h / 0 - 20 °C
10: 631 mg / CH2Cl2 / 4 h / Ambient temperature
11: sodium carbonate / dimethylformamide / 16 h / Ambient temperature
With
pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; trifluorormethanesulfonic acid; diphenyl phosphoryl azide; sodium carbonate; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine; lithium iodide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jm00001a015