7H-CYCLOPENTA[B]PYRIDIN-7-ONE, 5,6-DIHYDRO-

74701-35-2

31170-78-2

General procedure for the synthesis of 5,6-dihydro-7H-cyclopenta[b]pyridin-7-one from the compound (CAS: 74701-35-2): 5-benzylidene-6,7-dihydro-5H-[1]pyrazine (12.18 g, 58.8 mmol) was dissolved in 200 mL of mixed solvent of MeOH:CH2Cl2 (1:1), and the ozonolysis reaction was performed at 7 psi and 1.5 amperes for the ozonolysis reaction. Upon completion of the reaction, the reaction mixture was quenched with thiourea, filtered and concentrated. The product was purified by column chromatography using hexane:EtOAc (4:1) as eluent to afford 5.96 g (76% yield) of 5,6-dihydro-7H-cyclopenta[b]pyridin-7-one. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 2.75-2.82 (m, 2H), 3.15-3.22 (m, 2H), 7.47 (q, J = 4.40, 3.52 Hz, 1H), 7.91 (d, J = 8.79 Hz, 1H), 8.79 (d, J = 5.28 Hz, 1H).