Ammonia → HCID 11741227, compound

Participants

Reaction Steps

A pressure bottle containing sulfone 43 (320 mg, 0.703 mmol) was charged with tetrahydrofuran (40 mL), then chilled to <−40° C. in a dry ice/isopropanol bath. Ammonia gas (5.3 g, 0.31 mol) was then bubbled into the reaction. The pressure bottle was then sealed, and the reaction was allowed to warm to room temperature while stirring for 12 hours. The pressure was then released, and the reaction was concentrated under reduced pressure, dissolved in a minimum volume of CH2Cl2, then loaded onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 44: 158 mg (57%). 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 6H), 2.49 (m, 2H), 4.77 (m, 1H), 5.38 (m, 1H), 6.31 (d, J=5.4 Hz, 1H), 6.83 (bs, 2H), 7.04 (dd, J=7.2, 1.6 Hz, 1H), 7.28 (t, J=8.8 Hz, 2H), 7.60 (s, 1), 7.65 (m, 2H), 8.10 (d, J=5.4 Hz, 1H), 9.48 (d, J=7.2 Hz, 1H). MS (ESI+) 393.2.

Provenance & Evidence