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

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.

1. temperatureThe resulting solution was heated
2. temperatureat reflux overnight
3. customThe methanol was removed under reduced pressure
4. customleaving a light brown oil which
5. customwas partitioned between half-saturated sodium bicarbonate solution (50 mL) and ethyl acetate (75 mL)
6. extractionThe aqueous phase was extracted with additional ethyl acetate (50 mL)
7. washwashed with saturated aqueous sodium bicarbonate and brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification via silica chromatography (0-50% EtOAc/hexane)

ORD record

ord-e9833665d2f24f76851bbd74393f234d

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382197B2