Multi-step reaction with 11 steps
1: NaIO4 / ethanol; H2O / 16 h / -5 - 20 °C
2: 1.) nBuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, RT, 16 h
3: H2 / 10percent Pd/C / tetrahydrofuran / 16 h
4: pyridine / 1.5 h / 20 °C
5: NaN3 / dimethylformamide / 16 h / 100 °C
6: H2 / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature
7: 2-chloro-1-methylpyridinium iodide, n-tributylamine / CH2Cl2 / 2 h / Heating
8: H2 / Pd / tetrahydrofuran; propan-1-ol / 16 h / 40 °C
9: pyridine, 4-(dimethylamino)pyridine / 3 h / 40 °C
10: pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature
11: pTsOH*H2O / CH2Cl2; methanol / 2 h / Ambient temperature
With
pyridine; dmap; sodium periodate; n-butyllithium; sodium azide; tributyl-amine; 2-chloro-1-methyl-pyridinium iodide; hydrogen; toluene-4-sulfonic acid;
palladium on activated charcoal; palladium;
In
tetrahydrofuran; methanol; propan-1-ol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00012a018