Benzyl Bromide → HCID 86593353, compound

Participants

Reaction Steps

To a solution of methyl [(2R)-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]acetate (Example 1, Step 2, 299 mg, 1.36 mmol) in DMF (5 mL), Cs2CO3 (885 mg, 2.72 mmol) and then (bromomethyl)benzene (0.48 mL, 4.07 mmol) were added. After overnight stirring, the crude reaction mixture was poured into saturated NaHCO3 (50 mL) and extracted with EtOAc (3×50 mL). The combined organics were then washed with water (2×50 mL) and brine (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was subjected to silica gel chromatography eluting with 15%-25% EtOAc in Hexanes to give 131 mg (31%) methyl [(2R)-1-benzyl-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]acetate. LCMS (ES) 311.3 m/z (M+H)+.

Provenance & Evidence