Tributylphosphine → (R)-methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-hydroxyisonicotinate (459 mg, 3 mmol) and (S)-1-phenylethanol (366 mg, 3 mmol) in tetrahydrofuran (30 mL) was added dropwise a solution of tributylphosphine (909 mg, 4.5 mmol) in tetrahydrofuran (10 mL). The reaction solution was stirred at 0° C. for 0.5 hours. To the above solution was added 1,1′-(Azodicarbonyl)-dipiperidine (1134 mg, 4.5 mmol). The reaction mixture was stirred at 0° C. for 0.5 hours. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give (R)-methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylate as a white solid (451 mg, 58%).

Provenance & Evidence