methyl (E)-2-(tert-butoxycarbonylamino)-3-tetrahydropyran-4-yl-prop-2-enoate → methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate

Participants

Reaction Steps

A 250-mL pressure tube was charged with methyl (2E)-2-((tert-butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)-2-propenoate (8.75 g, 30.7 mmol), MeOH (100 mL), and rhodium[(1R,1′R,2R,2′R)-2,2′-bis(1,1-dimethylethyl)-2,2′,3,3′-tetrahydro-1,1′-bi-1H-isophosphindole-κP2,κP2′][(1,2,5,6-η)-1,5-cyclooctadiene]tetrafluoroborate (0.209 g, 0.30 mmol, ChiralQuest, Monmouth Junction, N.J.). The mixture was stirred under a 50 psi (344 kilopascal) hydrogen atmosphere for 3 h. The mixture was then filtered through a pad of silica, washing with 1:1 EtOAc in hexanes, and then concentrated to give methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate.

Provenance & Evidence