1-Ethynyl-4-fluorobenzene → HCID 59066524, compound

Participants

Reaction Steps

(±)-(4R*,5R*)-5-[(1R*)3-(4-Fluorophenyl) 1-hydroxyprop-2-ynyl]-1-methyl-4-phenylpyrrolidin-2-one was prepared from 4-fluorophenyl acetylene and Intermediate Z using a method analogous to that described for Examples 8. A solution of this compound (52 mg, 0.16 mmol) in EtOAc (5 mL) was added to a catalyst slurry prepared by addition of EtOAc (10 mL) to 10% Palladium on carbon (20 mg) under an Ar atmosphere. The reaction mixture was stirred under a H2 atmosphere (1 Atm) overnight. The resulting mixture was filtered through a pad of Celite® and the filtrate was concentrated under reduced pressure to give (±)-5-[(1R*)-3-(4-fluorophenyl)-1-hydroxypropyl](4R*,5R*)-1-methyl-4-phenylpyrrolidin-2-one (67 mg, 100%) as a white solid: mp 122-124° C.

Provenance & Evidence