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0 °C

6-(4-Methoxybenzyl)-2-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one (1 g, 4.49 mmol) from above was dissolved in a 1:1 mixture of DCM:MeOH, (50 mL) and cooled to −78° C. Ozone was bubbled through for 30 min. The reaction was warmed to 0° C. then NaBH4 (400 mg, 10.8 mmol) was added and the cold bath removed. After 10 min, the reaction mixture was quenched with Rochelle's Salt (20% solution, 50 mL) and diluted with EtOAc (100 mL). The organics were dried and concentrated to give 980 mg (96%). LC-MS (M+H)=299.1.

1. customOzone was bubbled through for 30 min
2. customthe cold bath removed
3. customthe reaction mixture was quenched with Rochelle's Salt (20% solution, 50 mL)
4. additiondiluted with EtOAc (100 mL)
5. customThe organics were dried
6. concentrationconcentrated
7. customto give 980 mg (96%)