HCID 118207375, compound → HCID 118207447, compound

Participants

Reaction Steps

A mixture of 3-(4-(4-(benzyloxy)phenyl)-3-hydroxypiperidin-1-yl)-1-(4-fluorobenzyl)-pyrrolidin-2-one (D2 from step E, 85 mg, 0.18 mmol), methanol (5 mL), and 38 mg 10% Pd/C was stirred in a pressure vessel overnight under 125 psi hydrogen pressure. The catalyst was removed by filtration through Celite and the filtrate was evaporated to dryness to yield 70 mg of racemic 1-(4-fluorobenzyl)-3-(cis-3-hydroxy-4-(4-hydroxyphenyl)-piperidin-1-yl)pyrrolidin-2-one. LCMS (method J) RT=0.63 (52% AP), 0.66 (31% AP) min, m/z 385.4 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.27-7.28 (m, 2H), 7.15-7.19 (m, 2H), 7.06 (d, J=8.4, 2H), 6.45 (d, J=8.4, 2H), 4.39 (d, J=15, 1H), 4.32 (d, J=15, 1H), 3.74-3.76 (m, 1H), 3.66 (m, 1H), 3.47 (m, 1H), 3.10-3.18 (m, 2H), 3.01 (m, 1H), 2.85-2.88 (m, 1H), 2.76 (m, 1H), 2.30-2.40 (m, 1H), 2.06-2.11 (m, 2H), 1.80-1.95 (m, 1H), 1.46 (d, J=12, 1H). The complete relative stereochemistry was not determined.

Provenance & Evidence