2-Nitropropane → 3-Methyl-1-(methylsulfonyl)-3-nitrobutane

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A solution of (methylsulfonyl)ethene (1.51 mL, 17.24 mmol, Sigma-Aldrich) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (3.86 ml, 25.9 mmol) in 2-nitropropane (72.8 mL, 810 mmol, Sigma-Aldrich) was stirred at RT for 2 d. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel) with 100% DCM followed by 1% 2 M NH3 in MeOH/DCM to give 3-methyl-1-(methylsulfonyl)-3-nitrobutane (338a, 2.45 g, 12.55 mmol, 73% yield) as a white solid. 1H NMR (400 MHz, DEUTERIUM OXIDE) δ ppm 1.31 (s, 6H) 2.08 (d, J=17.02 Hz, 1H) 2.08 (dd, J=4.30, 3.52 Hz, 1H) 3.05 (s, 3H) 3.33 (d, J=17.02 Hz, 1H) 3.33 (t, J=3.91 Hz, 1H).

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