Methanol → (R)-Methyl 4-(1-aminoethyl)benzoate

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Reaction Steps

To a solution of (R)-4-(1-amino-ethyl)-benzoic acid hydrochloride (0.20 g, 0.99 mmol) in methanol (3.2 mL) was added sulfuric acid (5.29 μL, 0.0992 mmol). The resulting solution was heated at reflux overnight. The methanol was removed under reduced pressure leaving a light brown oil which was partitioned between half-saturated sodium bicarbonate solution (50 mL) and ethyl acetate (75 mL). The aqueous phase was extracted with additional ethyl acetate (50 mL). The extracts were combined, washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification via silica chromatography (0-50% EtOAc/hexane) afforded product as a white solid (0.124 g, 70%). LC-MS: (FA) ES+ 180.

Provenance & Evidence