Pyridine → HCID 59066460, 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-fluorophenylacetylene and Intermediate Z using a method analogous to that described for Example 8. To a 300 mg (0.93 mmol)slurry of this compound in hexanes (60 mL) was added Pd on CaCO3 (80 Mg), followed by pyridine (0.23 mL, 2.8 mmol). The reaction mixture was stir-red overnight, then filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give (±)-(4R*,5R*)-5-[(2Z)(1R*)-3-(4-fluorophenyl)-1-hydroxyprop-2-enyl]-1-methyl-4-phenylpyrrolidin-2-one (302 mg, 100%) as a white solid: mp 163-165° C.; 1H NMR (CD3OD) δ 2.36 (dd, J=15.8, 7.8 Hz, 1H), 3.01-3.17 (m, 4H), 3.80-3.90 (m, 2H), 4.33 (d, J=8.7 Hz, 1H), 5.74 (dd, J=11.6, 8.8 Hz, 1H), 6.34 (d, J=11.6 Hz, 1H), 6.85-6.97 (m, 4H), 7.18-7.36 (m, 5H).

Provenance & Evidence