Diethyl Oxalate → HCID 11190201, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution of N-[3-(4-benzyl-piperazin-1-yl)-phenyl]-2,2-dimethyl-propionamide (2.4 g, 6.8 mmol) and N,N,N′N′-tetramethylethylenediamine (3.2 g, 27.4 mmol) in tetrahydrofuran (24 mL) was stirred for 15 minutes at 0° C., n-butyllithium (2.5M in hexane) (11 mL, 27.5 mmol) was added dropwise, and the mixture stirred for 3 hours at 15° C. The mixture was then cooled to −78° C., and diethyl oxalate (4.0 g, 27.4 mmol) was added. The mixture was stirred at −20° C. for 30 minutes, poured into a saturated aqueous solution of ammonium chloride (50 mL), and the product extracted into ethyl acetate (3×30 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to yield 4.5 g of crude product as a light brown oil. Purification by chromatography (150 g silica gel, 2% methanol in chloroform) afforded the title compound (1.5 g, 3.3 mmol, 49% yield) as a straw colored oil; this compound was confirmed by the following mass spectrometry results: EI M+ @ m/z 451 and (+)FAB [M+H]+ @ m/z 452, [M+Na]+ @ m/z 474.

Provenance & Evidence