Acetic Acid → 1-(4-butylphenyl)-3-cyclopropyl-5-hydroxypyridin-4(1H)-one

Participants

Reaction Steps

A suspension of 3-(benzyloxy)-1-(4-butylphenyl)-5-cyclopropylpyridin-4(1H)-one (27 mg, 0.07 mmol) and 10% Pd/C (1 mg, 0.001 mmol) in a 1:50 mixture of AcOH:MeOH was stirred under H2 (1 atra) for 18 h. The reaction mixture was filtered (0.5μ), concentrated under reduced pressure and purified by reversed phase HPLC (2 cm×5 cm CI 8, acetonitrile-water gradient, 0.05% TFA added) to provide 1-(4-butylphenyl)-3-cyclopropyl-5-hydroxypyridin-4(1H)-one, ′H NM (499 MHz, DMSO): δ 7.73 (s, 1H); 7.55 (d, J=2.7 Hz, 1H); 7.48 (d, J=8.1 Hz, 2H); 7.35 (d, J−8.1 Hz, 2H); 2.64 (t, J=7.7 Hz, 2H); 2.04-1.95 (m, 1H); 1.61-1.52 (m, 2H); 1.37-1.27 (m, 2H); 0.94-0.87 (m, 3H); 0.84-0.75 (m, 4H). HRMS (ES) calc (M+H)+=284.1645. found 284.1643.

Provenance & Evidence