Triacetoxyperiodinane → HCID 117732472, compound

Participants

Reaction Steps

Compound 21a (500 mg, 1.01 mmol) was placed in an 8 mL vial equipped with a stir bar and then DCM (2 mL) was added. Dess-Martin periodinane (471 mg, 1.11 mmol) was added as a solid and the reaction was stirred at rt for 20 min. The reaction was diluted with DCM (20 mL) and washed with saturated NaHCO3 solution (2×20 mL). The organic phase was dried over MgSO4 and filtered. The solvent was removed under reduced pressure. The crude product was chromatographed on a 40 g SiO2 pre-packed column eluting with 0-60% ACN/DCM to afford compound 21b. 1H-NMR (400 MHz, CDCl3) δ (ppm): 10.12 (s, 1H), 8.58 (d, J=2.2 Hz, 1H), 8.06 (d, J=5.6 Hz, 1H), 7.94 (dd, J=9.0, 2.4 Hz, 1H), 6.78 (d, J=8.8 Hz, 1H), 6.11 (d, J=5.9 Hz, 1H), 4.03-4.11 (m, 4H), 3.91-3.97 (m, 4H), 3.63-3.71 (m, 4H), 3.52-3.60 (m, 4H), 1.50 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H31N7O4: 494.3 (M+H). Found: 494.3.

Provenance & Evidence