2-Tert-butoxycarbonylamino-3-(2,5-difluorophenyl)-acrylic acid methyl ester → (R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2,5-difluorophenyl)propanoate

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Reaction Steps

To a solution of 2-tert-butoxycarbonylamino-3-(2,5-difluorophenyl)-acrylic acid methyl ester (4.9 g, 15.7 mmol) in methanol (49 mL) is added (−)-1,2-bis((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate (113 mg, 0.15 mmol), and is shaken for 20 h under an atmosphere of H2 at 75 psi. The suspension is filtered through Celite to remove catalyst and concentrated under reduced pressure to afford a light yellow solid. The solid is triturated in cold methanol to afford the title compound as a white solid (4.75 g, 15.4 mmol)

Provenance & Evidence