Multi-step reaction with 10 steps
1: acetyl chloride / 24 h / Ambient temperature
2: 70 percent / pyridine / 17 h / 50 °C
3: NaH / dimethylformamide / 3 h
4: H2O / acetic acid / 1 h / 70 °C
5: 90 percent / NaH / dimethylformamide / 2 h / 22 °C
6: 2.0 g / H2O / acetic acid / 6 h / Heating
7: 90 percent / NaBH4 / ethanol / 0.5 h / Ambient temperature
8: 81 percent / Et3N / 1,2-dichloro-ethane / 17 h / 20 °C
9: 82 percent / methyl trifluoromethanesulphonate / 1,2-dichloro-ethane / 3 h / Ambient temperature
10: 1.) H2; 2.) mercuric oxide, mercuric chloride / 1.) 1,6-cyclooctadiene-bis-(methyldiphenylphosphine)-iridium hexafluorophosphate / 1.) 1,2 dichloroethane, 3 h, RT; 2.) acetone/H2O, 20 min, RT
With
pyridine; sodium tetrahydroborate; water; hydrogen; sodium hydride; triethylamine; acetyl chloride; methyl trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide;
1.) 1,6-cyclooctadiene-bis-(methyldiphenylphosphine)-iridium hexafluorophosphate;
In
ethanol; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89206-1