Sodium borohydride → HCID 69547774, compound

Participants

Reaction Steps

To an ethanol solution (5 mL) of 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl)-phenyl]-3-oxo-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester (124 mg, 0.24 mmol)was added NaBH4 (36 mg, 0.96 mmol). The reaction mixture was stirred for 2.25 h and then concentrated to dryness. The residue was dissolved in ethyl acetate and washed with NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to provide 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl)-phenyl]-3-hydroxy-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester. To a methanol solution (5 mL) of 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl-phenyl]-3-hydroxy-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester was added an aqueous solution (2.5 mL) of LiOH monohydrate (46 mg, 1.09 mmol). The reaction mixture was stirred for 6 h and then concentrated to remove the methanol. The aqueous concentrate was diluted with CH2Cl2 and 1 N HCl was added, extracted with CH2Cl2 and dried over MgSO4. This mixture was filtered and concentrated to yield 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl)-phenyl]-3-hydroxy-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid (116 mg, 0.23 mmol) as an oil.

Provenance & Evidence