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ChemicalBook CAS DataBase List Hydroxypioglitazone
146062-44-4

Hydroxypioglitazone synthesis

10synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 9 steps
1: NaH / dimethylformamide; toluene / 2.5 h / 80 °C
2: 10percent aq. H2SO4 / 2 h / Heating
3: 90 percent / NaBH4 / ethanol / 1.5 h / 0 °C
4: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT
5: 27 percent / H2O / 5 h / 160 °C
6: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature
7: 58 percent / piperidine / ethanol / 18 h / Heating
8: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature
9: 98 percent / 2N aq. HCl / methanol / 2 h / Heating

References:

Tanis, Steven P.;Parker, Timothy T.;Colca, Jerry R.;Fisher, Roberta M.;Kletzein, Rolf F. [Journal of Medicinal Chemistry,1996,vol. 39,# 26,p. 5053 - 5063]

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