Multi-step reaction with 12 steps
1: NaH / tetrahydrofuran / 2 h / 0 °C
2: AcOH / methanol / 6 h / 40 °C
3: imidazole / dimethylformamide / 10 h / Ambient temperature
4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C
5: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature
6: NaOCl / CH2Cl2 / 4 h / Ambient temperature
7: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature
8: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C
9: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h
10: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether
11: CrO3, H+
With
pyridine; 1H-imidazole; chromium(VI) oxide; sodium hypochlorite; hydroxylamine hydrochloride; hydrogen; boric acid; pyridinium p-toluenesulfonate; hydrogen cation; sodium hydride; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00258a051