Acetone → N-(2-Acetyl-phenyl)-2,3-dihydroxy-3-methyl-butyramide

Participants

Reaction Steps

To the product of Example 10 (440 mg, 2.03 mmol) in acetone (4 mL) and H2O (1 mL) was added 4-methylmorpholine N-oxide (269 mg, 2.23 mmol), and 2.5 wt % OsO4 (0.25 mL, 0.02 mmol). The reaction mixture was stirred at room temperature for 26 h. EtOAc was added to the reaction mixture, and the resulting solution was washed with aqueous sodium bisulfite, brine and dried over MgSO4. After evaporation of the volatiles, the crude product (505 mg, 99% yield) was clean enough to carry on the next step. 1H NMR (360 MHz, CDCl3) δ 8.69-8.61 (m, 1H), 7.85-7.77 (m, 1H), 7.75-7.42 (m, 1H), 7.12-7.04 (m, 1H), 4.88 (d, J=5.4 Hz, 1H), 4.10 (s, 1H), 4.07 (d, J=5.4 Hz, 1H), 2.57 (s, 3H), 1.27 (s, 3H), 1.25 (s, 3H).

Provenance & Evidence