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0 °C

To a solution of 3-(3-nitropyridin-4-yl)cyclohex-2-en-1-one (1.9 g, 8.7 mmol) and cerium trichloride (4.2 g, 11 mmol) in EtOH (30 mL) at 0° C., sodium tetrahydroborate (0.43 g, 11 mmol) was slowly added. The reaction mixture was stirred at 0° C. for 2 h, then quenched with water (40 mL). After vacuum filtration, the residue was diluted with EtOAc. The aqueous layer was extracted three times with EtOAc. The combined organic layers were dried, filtered and concentrated under reduced pressure to give a crude product, which was further purified by silica gel column chromatography (eluting with 0-30% MeOH in EtOAc) to give the sub-title compound (1.06 g, 55%). LCMS calc. for C11H13NO3 (M+H)+: m/z=221.1. Found: 221.1.

1. customquenched with water (40 mL)
2. filtrationAfter vacuum filtration
3. additionthe residue was diluted with EtOAc
4. extractionThe aqueous layer was extracted three times with EtOAc
5. customThe combined organic layers were dried
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto give a crude product, which
9. customwas further purified by silica gel column chromatography (eluting with 0-30% MeOH in EtOAc)