Cesium carbonate → (+/-)-tert-butyl (1R,5S,6S)-5-methyl-6-(2-(methylsulfonyl)ethoxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

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A mixture of (+/−)-Tert-butyl (1R,5S,6S)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.), methylsulfonylethene (30.0 equiv.) and CESIUM CARBONATE (1.2 equiv.) in t-BuOH (0.22 M) was stirred at 22° C. for 5 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 (+/−)-tert-butyl (1R,5S,6S)-5-methyl-6-(2-(methylsulfonyl)ethoxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate in 84% yield. LC/MS (m/z)=456.2 (MH+), Rt=0.87 min. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.10 (d, J=6.60 Hz, 3H), 1.47 (s, 9H), 1.92-2.16 (m, 2H), 2.17-2.32 (m, 1H), 2.93-3.00 (m, 1H), 3.09 (s, 3H), 3.18 (d, J=14.87 Hz, 1H), 3.38-3.52 (m, 1H), 3.63 (d, J=2.40 Hz, 1H), 3.95-4.06 (m, 1H), 4.21 (td, J=9.84, 2.42 Hz, 1H), 4.56 (d, J=7.58 Hz, 1H), 5.58 (br. s., 1H), 5.66 (d, J=9.44 Hz, 1H), 7.20 (d, J=4.99 Hz, 1H), 8.73 (d, J=4.99 Hz, 1H), 9.05 (s, 1H).

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