Sodium borohydride → HCID 67490895, compound

Participants

Reaction Steps

Cerium (III) chloride heptahydrate (57.0 g, 153 mmol) was dissolved in ethanol (700 mL). Sodium borohydride (5.79 g, 153 mmol) was added at 0° C., and the mixture was stirred for 10 minutes. A solution of (3S,4R)-1-benzyloxycarbonyl-4-(1-formylvinyl)pyrrolidine-3-carboxylic acid tert-butyl ester (55.0 g, 153 mmol) in ethanol (700 mL) was added dropwise to the reaction solution at 0° C., and the mixture was stirred at room temperature for three hours. The reaction solution was extracted with a 10% citric acid solution, water, and ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=24:1→2:1) to give 42.2 g of the title compound as a colorless oil.

Provenance & Evidence