Water → HCID 86607428, compound

Participants

Reaction Steps

To a suspension of intermediate 5.1 (580 mg, 1.41 mmol) in anhydrous THF (20 mL) at −5° C. was added n-BuLi (0.97 mL, 1.6 M, 1.55 mmol) in hexane dropwise under Ar. The mixture was stirred for 20 min after addition was complete. To the reaction mixture was then added a solution of methyl 4-{2-[(2R)-2-formyl-5-oxopyrrolidin-1-yl]ethyl}benzoate (intermediate 1.4) (388 mg, 1.41 mmol) in anhydrous THF (4 mL) dropwise. The stirring was continued for 1 hr. Water was added to quench the reaction and the mixture was concentrated in vacuo to remove most of the THF. Extraction with ethyl acetate, washing organic phase with brined, drying and concentration afforded the crude product mixture containing cis and trans compounds as a pale oil, which was used directly for step without further purification.

Provenance & Evidence