Ethyl Acetate → 7-Chloro-1-cyclopropyl-6-fluoro-1,2,3,4-tetrahydroquinoxaline

Participants

Reaction Steps

To a suspension of 390 mg (1.532 mmol) 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-quinoxaline-2,3-dione in 20 mL tetrahydrofuran was added 3.37 mL (3.369 mmol) 1M borane tetrahydrofuran complex. The reaction mixture was stirred for 6 hours at room temperature. The reaction mixture was poured on 30 mL 10% aqueous sodium bicarbonate solution and 30 mL ethyl acetate. The mixture was stirred for 30 min. at room temperature and the layers were separated. The aqueous layer was extracted a second time with 30 mL ethyl acetate. The organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 40:60) to give 211 mg (61%) of the desired compound as a white solid. MS (ESI): m/z=225.0 [M+H]+.

Provenance & Evidence