Ethanol → HCID 67490764, compound

Participants

Reaction Conditions

Reaction Steps

Lithium borohydride (4.96 g, 0.228 mol) was suspended in tetrahydrofuran (500 mL). A solution of (3R)-3-allyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (50.0 g, 0.152 mol) in tetrahydrofuran (100 mL)-ethanol (17.7 mL) was added to the suspension using a dropping funnel over 10 minutes. The mixture was heated to 40° C., stirred for 12 hours, and then heated to reflux for 20 hours. After cooling to 0° C., a saturated ammonium chloride solution (100 mL) was carefully added. After the tetrahydrofuran component was evaporated under reduced pressure, the reaction solution was poured into a mixture of ethyl acetate (100 mL) and a saturated ammonium chloride solution (100 mL), followed by extraction with ethyl acetate (1000 mL, 750 mL). The organic layers were combined and washed with brine (200 mL). After drying over anhydrous sodium sulfate and filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4) to give 29.9 g (76%) of the title compound as a colorless viscous oil.

Provenance & Evidence