Dimethylformamide → HCID 178501093, compound

Participants

Reaction Conditions

Reaction Steps

Racemic methyl trans-4-[1-(5-bromopyridin-2-yl)hydroxyethyl]cyclohexanecarboxylate (500 mg, 1.461 mmol) was dissolved in DMF (7.3 mL) and cooled to 0° C. Sodium hydride (60 wt %, 117 mg, 2.92 mmol) was added in one portion. The mixture was stirred and allowed to warm to room temperature. After 20 minutes, methyl iodide (0.183 mL, 2.92 mmol) was added, and the reaction was stirred at room temperature for 30 minutes. The mixture was diluted with water, ethyl acetate, and brine. The layers were separated, and the organic portion dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel column chromatography (20% EtOAc:hexanes) gave racemic methyl trans-4-[1-(5-bromopyridin-2-yl)-1-methoxyethyl]cyclohexanecarboxylate as a colorless oil. MS ESI calcd. for C16H23BrNO3 [M+H]+ 356 and 358. found 356 and 358. 1H NMR (500 MHz, DMSO-d6) 8.64 (d, J=2.2 Hz, 1H), 8.01 (dd, J=2.3, 8.5 Hz, 1H), 7.37 (d, J=9.1 Hz, 1H), 3.54 (s, 3H), 2.98 (s, 3H), 2.20-1.50 (m, 5H), 1.55 (s, 3H), 1.40-0.75 (m, 5H).

Provenance & Evidence