Tetrahydrofuran → 3,4-Dimethyl-1-[(S)-3-(3-fluorophenyl)-4-(4-methoxyphenyl)butanoyl]-5-phenylimidazolidin-2-one

関与物質

反応条件

反応手順

A solution of 4-methoxyphenylmagnesium bromide in THF (0.31 M, 14.7 mL, 4.56 mmole) was added dropwise to a stirred suspension of (4 R, 5 S)-3,4-dimethyl-1-[(E)-3-(3-fluorophenyl)prop-2-enoyl]-5-phenylimidazolidin-2-one (514 mg, 1.52 mmole), CuBr.DMS complex (229 mg, 1.06 mmole), and ZnI2 (582 mg, 1.82 mmole) in THF/toluene (10 mL) at −15° C. After 1.5 hr the reaction was quenched with saturated NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4 and concentrated to dryness. The residue was taken up in 1:1 Et2O/hexanes and cooled at −20° C. for 18 hr. The solid was collected, washed with 1: Et2O/hexanes, and dried in vacuum to afford a first crop of the title compound. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (30% EtOAc/hexanes) to afford additional title compound as a yellow oil that solidified in vacuum. The total yield of the title compound was 0.62 g(91%): 1HNMR (300 MHz, CDCl3) δ 6.75-7.37 (m, 13 H), 5.10 (d, J=8.5 Hz, 1 H), 3.80 (s, 3 H), 3.65-3.85 (m, 1 H), 3.63 (dd, J=16.7, 9.6 Hz, 1 H), 3.36-3.41 (m, 1H), 3.14 (dd, J=16.7, 4.9 Hz, 1 H), 2.72-2.88 (m, 2 H), 2.79 (s, 3 H), 0.74 (d, J=6.6 Hz, 3 H).

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