Citric Acid → HCID 67490989, compound

Participants

Reaction Conditions

Reaction Steps

Lithium borohydride (1.174 g, 53.90 mmol) was added to a solution of 1-[(3R)-5-oxo-1-[(1S)-1-phenylethyl]pyrrolidin-3-yl]cyclopropanecarboxylic acid ethyl ester [see Journal of Medicinal Chemistry, Vol. 46, No. 6, p. 1005 (2003)] (2.03 g, 6.74 mmol) in tetrahydrofuran (20 mL). The mixture was heated with stirring on an oil bath at 70° C. for 30 hours. After cooling to room temperature, the reaction solution was poured into an ice-cooled 10% citric acid solution (80 mL), followed by extraction with ethyl acetate (200 mL). The organic layer was washed with water (80 mL) and brine (80 mL), dried over anhydrous sodium sulfate, and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2→1:1→2:1→1:0→chloroform:methanol=9:1) to give 1.30 g (74%) of the title compound as a colorless transparent gummy solid.

Provenance & Evidence