Water → tert-butyl[7-(3,4-dihydroxycyclopentyl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate

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Reaction Steps

To a solution of tert-butyl [7-(cyclopent-3-en-1-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate (Compound 243C: 33 mg, 0.10 mmol) in t-BuOH (1 mL) and H2O (1 mL) were added N-methylmorpholine N-oxide (14 mg, 0.12 mmol) and potassium osmate dihydrate (0.37 mg, 0.0010 mmol). The resulting mixture was stirred at rt overnight. The mixture was diluted with EtOAc (30 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure to give the title compound as a white solid, 36 mg, 99% yield. 1H NMR (CDCl3): 1.52 (s, 9H), 1.90-1.94 (m, 2H), 2.14-2.19 (m, 2H), 2.34 (br s, 2H), 3.17 (s, 3H), 3.56 (m, 1H), 4.33 (s, 2H), 4.39 (m, 2H), 7.26 (d, J=8.6 Hz, 1H), 8.14 (d, J=8.6 Hz, 1H), 9.50 (br s, 1H). MS (ES+): m/z=363.16 [MH+]. HPLC: tR=3.44 min (ZQ3, polar—5 min).

Provenance & Evidence