HCID 67490821, compound → HCID 67490975, compound

Participants

Reaction Steps

A hydrogen fluoride-pyridine complex (10 mL) was added dropwise to a solution of (3R)-3-[1-(tert-butyldiphenylsiloxymethyl)cyclopropan-1-yl]-5-oxo-1-[(1S)-1-phenylethyl]pyrrolidin-4-ylcarboxylic acid ethyl ester (2.81 g, 4.93 mmol) in pyridine (20 mL) at 0° C. over five minutes. The mixture was stirred at room temperature for 2.5 hours and then poured into ice water (150 mL), followed by extraction with ethyl acetate (300 mL). The resulting organic layer was washed with a 10% citric acid solution (100 mL), water (100 mL), and brine (100 mL) and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2→1:1→2:1) to give 1.378 g (84%) of the title compound as a pale yellow gummy solid.

Provenance & Evidence