Water → HCID 59846309, compound

Participants

Reaction Steps

To a solution of (R)-2,2,2-trifluoro-N-(7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (3.51 g, 13.4 mmol, 1 equiv) in acetone (217 mL) was added magnesium sulfate heptahydrate (9.92 g, 40.3 mmol, 3 equiv) with water (167 mL). The mixture was stirred in ice bath. Potassium permangnate (6.37 g, 40.3 mmol, 3 equiv) was added in portions within 1 hour period. After addition, the reaction mixture was stirred at RT for 16 h. The resulting black solid was filtered off and washed with acetone. The combined filtrate and washings were diluted with CH2Cl2 (200 mL). The aqueous phase was separated and washed with CH2Cl2. The CH2Cl2 solution was washed with saturated Na2S2O7 solution (150 mL). The resulting black solid was filtered off The filtrate was evaporated to remove organic solvents. The concentrate was diluted with CH2Cl2 (400 mL). The aqueous phase was separated and washed with CH2Cl2. The combined CH2Cl2 phase was concentrated to give a white solid product (3.54 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ 10.00 (s, 1H), 8.00 (q, 1H), 7.30-7.36 (m, 1H), 7.15 (dd, 1H), 5.32-5.38 (m, 1H), 2.60-2.85 (m, 2H), 2.16-2.30 (m, 2H).

Provenance & Evidence