Metaperiodic acid → HCID 57659749, compound

Participants

Reaction Conditions

Reaction Steps

To periodic acid (176 mg, 0.770 mmol) in CH3CN (2 mL) was added chromium(III) oxide (2.1 mg, 0.021 mmol). The reaction was stirred several minutes until it turned fluorescent orange and all solids were dissolved. The reaction was cooled to 0° C. and a solution of (R)-4-cyclopropyl-5-(4-(trifluoromethyl)phenylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole (12) (50 mg, 0.14 mmol) in CH3CN (1 mL) was added. The reaction was stirred for 1 hr until TLC monitoring showed the disappearance of starting material. The reaction was filtered through a plug of Celite and concentrated in vacuo. The residue was taken up in EtOAc (2 mL) and washed with water (2 mL), 5% NaHSO3 (2 mL), brine (2 mL), dried over Na2SO4, and concentrated in vacuo. The resulting crude product was purified via column chromatography using EtOAc/hexane gradients to yield (R)-4-cyclopropyl-5-(4-(trifluoromethyl)phenylsulfonyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (23) (15 mg, 28%) as a white solid.

Provenance & Evidence