Potassium trimethylsilanolate → [2-(1-{[(3S,4R)-1-Tert-Butyl-4-(2,4-Difluorophenyl)Pyrrolidin-3-yl]Carbonyl}Piperidin-4-yl)-5-Chlorophenyl]Acetic Acid

Participants

Reaction Steps

Potassium trimethylsilanolate (0.900 g, 7.05 mmol) was added to a stirred solution of methyl [2-(1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-piperidin-4-yl)-5-chlorophenyl]acetate (1-9) (1.25 g, 2.35 mmol) in tetrahydrofuran (24 mL) at room temperature. After approximately 15 h, the volatiles were evaporated in vacuo and the crude residue was treated with a saturated solution of hydrogen chloride in ethyl acetate. After approximately 5 min, the reaction mixture was concentrated under reduced pressure and the crude residue triturated twice with dry diethyl ether to give 1-10 as an amorphous white solid (m/z (ES) 519 (MH+).

Provenance & Evidence