Methylparaben → HCID 17859366, compound

Participants

Reaction Steps

In THF (100 ml) was dissolved N-(tert-butoxycarbonyl)-2-(methylamino)ethanol (3.03 g, 17.3 mmol). To the resulting solution was added methyl 4-hydroxybenzoate (2.77 g, 18.2 mmol) and under stirring at 0° C. in a nitrogen gas stream, triphenylphosphine (6.35 g, 24.2 mmol) and DIAD (3.5 ml, 24.5 mmol) were added. The resulting mixture was stirred further at room temperature for 18 hours. From the reaction mixture, the solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (4:1, v/v) eluate fractions, methyl 4-(2-(N-(tert-butoxycarbonyl)-N-methylamino)ethoxy)benzoate (4.09 g, 76%) was obtained as a yellow oil. The resulting compound (933 mg, 3.01 mmol) was dissolved in methylene chloride (3 ml). To the resulting solution was added trifluoroacetic acid (1 ml) under stirring at 0° C. The reaction mixture was stirred further at room temperature for 2 hours. From the reaction mixture, the solvent was distilled off under reduced pressure. The residue was neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with a chloroform-methanol mixture (5:1, v/v). The extract was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent, whereby methyl 4-(2-(N-methylamino)ethoxy)benzoate (618 mg, 98%) was obtained as a yellow oil.

Provenance & Evidence