Sodium borohydride → HCID 59075085, compound

Participants

Reaction Steps

Sodium borohydride (37 mg, 0.98 mmol) was slowly added to a solution of 7-{(R)-3,3-dimethyl-2-oxo-5-[(E)-3-oxo-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-pyrrolidin-1-yl}-heptanoic acid ethyl ester (280 mg, 0.61 mmol) in methanol (4 mL) at −20° C. The reaction flask was kept at −10° C. for 45 minutes. When the addition was complete the reaction vessel was kept at −10 C for 40 min. When the reaction was done, it was quenched with acetone and concentrated to dryness. The residue was dissolved in ethyl acetate, washed with brine and dried. After concentration, the crude mixture was purified on a silica gel column using hexane:ethyl acetate 1:1 as the solvent, giving 90 mg of 7-{(R)-5-[(E)-3-hydroxy-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-3,3-dimethyl-2-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester.

Provenance & Evidence