Methyl Acrylate → HCID 86705260, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (+/−)-tert-butyl (1R,5S,6R)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.), methyl acrylate (30.0 equiv.) and CESIUM CARBONATE (1.2 equiv.) in t-BuOH (0.38 M) was stirred at 35° C. for 16 hrs. The reaction was cooled to room temperature, followed by the addition of NaHCO3(aq.) and water. The mixture was extracted with EtOAc and the combined organics were dried over MgSO4, filtered, and concentrated. The sample was purified by ISCO chromatography to yield (+/−)-methyl 3-((1R,2R,6S)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyloxy)propanoate in 48% yield. LC/MS (m/z)=436.1 (MH+), Rt=0.91 min.

Provenance & Evidence