Toluene → HCID 58909951, compound

Participants

Reaction Steps

Tetra-n-butylammonium bromide (227 mg, 0.704 mmol) and methyl iodide (0.18 ml, 2.9 mmol) were added to a mixed solvent of 1-{3-(tert-butyl)-5-[(3R,4R)-3-hydroxy-4-(methoxymethoxy)tetrahydro-1H-1-pyrrolyl]-4-methoxyphenyl}-1-ethanone (496 mg, 1.41 mmol) in a toluene (3 ml) −50% aqueous NaOH (3 ml) mixed solvent in that order at room temperature and the mixture was stirred for 64 hours. It was then diluted with water, extraction was performed with ethyl acetate and the extract was washed with brine. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (397 mg, 77%) as a light yellow oil.

Provenance & Evidence