Potassium Persulfate → HCID 86654010, compound

Participants

Reaction Steps

tert-Butyl {2-methyl-3-oxo-7-[(E)-2-phenylethenyl]-2,3-dihydro-1H-isoindol-4-yl}carbamate (Compound 109D, 1.0E2 mg, 0.27 mmol) was added in one portion to a pre-stirred mixture (room temperature, 45 min) of potassium osmate dihydrate (1.0 mg, 0.0027 mmol) and potassium monopersulfate (170 mg, 1.1 mmol) in DMF (1.35 mL). After stirring overnight at room temperature, the reaction mixture was treated with 1.35 mL of saturated aqueous Na2SO3. The resulting slurry was extracted with EtOAc (3×) and the combined organic layers were washed with 1N HCl (3×) and brine and concentrated in vacuo. The desired product was obtained after chromatography using an ISCO Combiflash unit (0-15% EtOAc in Heptane) as 23 mg of a tan solid (29% yield). 1H NMR (400 MHz, DMSO-d6) δ=1.51 (s, 9 H), 3.08 (s, 3 H), 4.74 (s, 2 H), 8.12 (d, J=8.6 Hz, 1 H), 8.21 (d, J=8.6 Hz, 1 H), 9.95 (s, 1 H), 10.01 (s, 1 H). MS (ES+): m/z 291.28 (100) [MH+]; HPLC: tR=1.27 min (UPLC, Analytical).

Provenance & Evidence