Chloromethyl Methyl Ether → HCID 58910015, compound

Participants

Reaction Steps

Diisopropylethylamine (2.3 ml, 13 mmol) was added to a solution of the 1-{3-(tert-butyl)-5-[(3R,4R)-3,4-dihydroxytetrahydro-1H-1-pyrrolyl]-4-methoxyphenyl}-1-ethanone (1.32 g, 4.29 mmol) in methylene chloride (10 ml) while cooling on ice, and then MOMCl (0.49 ml, 6.5 mmol) was added dropwise and the mixture was stirred at the same temperature for 10 minutes and then at room temperature for 2.5 hours. After completion of the reaction, it was diluted with water and extraction was performed with ethyl acetate. After washing with brine and drying over 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 (496 mg, 33%) as a light yellow oil.

Provenance & Evidence