Ethyl Acetate → HCID 66725157, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of sodium periodate (607 mg, 2.85 mmol) in water (3.8 mL) was added a catalytic amount of RuCl3(III) (27 mg, 0.13 mmol) followed by ethyl acetate (10 mL) and acetonitrile (10 mL). The reaction mixture was stirred for 5 min at 0° C. before (4R)-4-(4-chloro-2-vinylphenyl)pyrrolidin-2-one prepared as described above was added. After stirring for an additional two minutes, the reaction mixture was quenched with a Na2S2O3 aq. solution (2 M, 10 mL). The layers were separated and the aqueous phase was extracted with ethyl acetated (4×20 mL). The combined organic phases were dried over MgSO4 and concentrated in vacuo. The resulting crude (2-((3S)-5-oxopyrrolidin-3-yl)-5-chlorobenzaldehyde was dissolved in tetrahydrofuran/water (v/v 1:1, 4.5 mL) and sodium borohydride (70 mg, 1.85 mmol) was added. The mixture was stirred for 20 min at room temperature and then diluted with water (7 mL), extracted with dichloromethane (4×30 mL). The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude residue was then treated with a 6N HCl aqueous solution (1.5 mL) and heated overnight at 90° C. The final product was purified by HPLC to provide the title compound. 1H-NMR (400 MHz, CD3OD): δ 2.84-2.70 (m, 2H), 3.08-3.14 (m, 1H), 3.75-3.83 (m, 1H), 4.85 (s, 1H), 4.57-4.60 (d, J=12.0 Hz, 1H), 7.33-7.42 (m, 3H); MS (ESI) m/z 244.06 (M+H)+.

Provenance & Evidence