Acetic Acid → HCID 57809903, compound

Participants

Reaction Steps

To a solution of 2-(3,4-dihydro-2H-quinoxalin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (Example 4) (18.6 mg) in acetonitrile (3 mL) was added formaldehyde solution (37% w/w aqueous, 300 μL) followed by sodium cyanoborohydride (13.8 mg). After 30 minutes at room temperature, acetic acid (50.4 μL) was added. The resulting mixture was stirred for 3 hours, quenched with saturated aqueous sodium bicarbonate solution and extracted three times with methylene chloride. The combined organic phases were dried over sodium sulfate, filtered, and the volatiles removed in vacuo. The residue was purified by preparative TLC (eluted with 25% EtOAc-hexanes) to give the title compound as a pale yellow oil (16.6 mg).

Provenance & Evidence