Triacetoxyperiodinane → (1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

Participants

Reaction Steps

To a solution of (1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanol (81 mg, 0.196 mmol) in dichloromethane (6 ml) was added Dess-Martin periodinane (125 mg, 0.295 mmol). The reaction mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was partitioned between dichloromethane and 2:1 saturated aqueous NaHCO3:10% aqueous Na2S2O3. The organic layers were collected, dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography using 20-50% EtOAc in hexanes as eluant to provide 18 mg (22%) of (1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as an off white solid. MP 246-247° C., M+H=439.

Provenance & Evidence