Hydrochloric Acid → 4-(R)-(2-Furyl)carbonyl-1-[1-(R)-phenylethyl]-2-pyrrolidone

Participants

Reaction Steps

In an atmosphere of nitrogen, 0.5 mol/1 of 2-furylmagnesium bromide (180 ml) prepared from furan was added dropwise to a tetrahydrofuran solution (160 ml) of N-methyl-N-methoxy-1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-carboxamide (8.30 g, 30.0 mmol), and the mixture was stirred for 30 minutes. The reaction solution was mixed with 1 mol/1 hydrochloric acid (200 ml) under ice-cooling and extracted with ethyl acetate (200 ml×2), and then the organic layer was washed with saturated brine (100 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was applied to a silica gel column chromatography. By eluting with a n-hexane:ethyl acetate system of from (1:1) to (1:2), 3.94 g (46%) of the title compound was obtained as a light yellow oil. 1H-NMR (400 MHz, CDCl3) δ: 1.55 (3 H, d, J=6.84 Hz), 2.72-2.87 (2 H, m), 3.20-3.25 (1 H, m), 3.67 (1 H, dd, J=6.83, 9.77 Hz), 3.80-3.89 (1 H, m), 5.53 (1 H, q, J=6.84 Hz), 6.57 (1 H, dd, J=1.46, 3.42 Hz), 7.18-7.38 (6 H, m), 7.60 (1 H, d, J=0.98 Hz).

Provenance & Evidence