Sodium Sulfate → HCID 86585350, compound

Participants

Reaction Steps

To a solution of (±)-N-[2-[2-(2,3-dihydroxy-1,1-dimethylpropyl)-1H-indol-3-yl]ethyl]-carbamic acid phenylmethyl ester (0.323 g, 0.81 mol) in 1:1 acetone/CH2Cl2 (19.5 mL) was added NaIO4 (0.350 g, 1.64 mmol) in H2O (2.2 mL). The reaction mixture was stirred for 3 h at rt. Solid Na2SO4 was added. The mixture was filtered. The filtrate was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to an oil. This oil was purified by silica chromatography to give the title compound: TLC Rf=0.31 (1:1 heptane/EtOAc); MS (ESI+) m/z 365.2; 1H NMR (300 MHz, CDCl3) δ 9.56 (1H), 8.11 (1H), 7.64 (1H), 7.37 (5H), 7.21 (1H), 7.13 (1H), 5.14 (2H), 4.92 (1H), 3.45 (2H), 2.95 (2H), 1.60 (6H).

Provenance & Evidence