Sodium Thiosulfate → HCID 86703314, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-(6-hydroxymethylpyridin-2-ylmethyl)-6-methoxy-2-phenyl-1H-indole-1-carboxylate (600 mg) in dichloromethane (6 mL) was added Dess-Martin periodinane (744 mg), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1 mol/L aqueous sodium thiosulfate solution, followed by stirring for 5 minutes. The mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (486 mg). 1H-NMR (CDCl3) δ ppm: 1.23 (9H, s), 3.89 (3H, s), 4.15 (2H, s), 6.84 (1H, dd, J=2.3, 8.7 Hz), 7.15-7.21 (1H, m), 7.28-7.44 (6H, m), 7.61-7.69 (1H, m), 7.72-7.77 (1H, m), 7.86 (1H, d, J=2.3 Hz), 10.02-10.05 (1H, m).

Provenance & Evidence