O-Cresol → HCID 42644120, compound

Participants

Reaction Steps

(5-Hydroxymethyl-thiophen-3-yl)-piperidin-1-yl-nnethanone (0.068 g, 0.3 mmol) was dissolved in THF (5 mL). Triphenylphosphine (0.3 mmol), diethylazodicarboxylate (0.3 mmol) and 2-methyl-phenol (0.3 mmol) were added and the reaction stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride and the solvent was reduced under vacuum. The residue was partitioned between DCM and water and the organic solution separated, dried over magnesium sulphate, filtered and the solvent evaporated. The product was purified by HPLC, eluting with acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (20 mg). LCMS m/z 316.20 [M+H]+RT=11.75 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 7.45 (s, 1H), 7.2-7.1 (m, 3H), 6.9 (m, 2H), 5.2 (s, 2H), 3.6 (m, 4H), 2.25 (s, 3H), 1.7-1.6 (m, 6H).

Provenance & Evidence