Trichloroisocyanuric Acid → HCID 86601041, compound

Participants

Reaction Steps

A solution of (1R,3S,4S)-3((S)-2-tert-Butoxycarbonyl-1-hydroxymethyl-ethylcarbamoyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester (1.1 g) in DCM (10 ml) was cooled to 0° C. under nitrogen. 2,2,6,6-tetramethylpiperidinyloxy (TEMPO, 4 mg) was then added followed by trichloroisocyanuric acid (621 mg) portionwise over 30 minutes. The mixture was stirred at ambient temperature for 1 hour, then filtered through celite. The filtrate was washed with water, 1M sodium thiosulfate solution and brine. Drying over magnesium sulfate and concentration under reduced pressure gave the sub-title compound as a colorless oil (698 mg, 64%); 1H NMR (400 MHz, d-6 DMSO) δ 1.16-1.89 (16H, m), 2.30-2.80 (2H, m), 3.68-3.81 (1H, m), 4.19 (1H, brm), 4.39 (1H, m), 4.91-5.16 (2H, m), 7.21-7.43 (5H, m), 8.45 (0.4H, d), 8.60 (0.6, d), 9.19 (0.6H, S), 9.37 (0.4H, s).

Provenance & Evidence