3-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one → 3-Hydroxy-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one

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Reaction Steps

3-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one (131 mg, 0.350 mmol) was hydrogenated (balloon) with 10% Pd/C (37 mg, 0.035 mmol) in MeOH (3 mL) at RT. After stirring overnight the mixture was filtered using a 0.45 μm PTFE syringe filter then purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-50% CH3CN/water over 20 min at 20 mL/min) to give the title compound (59 mg, 59%) as an off-white solid. 1H NMR (500 MHz, CDCl3): δ 7.52 (d, J=2.6 Hz, 1 H); 7.40-7.28 (m, 5 H); 6.98 (d, J=2.6 Hz, 1 H); 4.08 (t, J=8.4 Hz, 1 H); 3.77-3.66 (m, 2 H); 3.64 (s, 3 H); 2.99 (m, 1 H); 2.76 (m, 1 H). HRMS (ES) calc (M+H)+=285.1234, found 285.1228.

Provenance & Evidence