[C@@H:1]12[CH2:8][C:7](=[O:9])[CH2:6][C@@H:5]1[CH2:4][C:3](=[O:10])[CH2:2]2.[N-:11]=[N+]=[N-].[Na+].[OH-].[Na+]>Cl>[CH2:4]1[C@H:5]2[CH2:6][C:7](=[O:9])[CH2:8][C@H:1]2[CH2:2][C:3](=[O:10])[NH:11]1(cis)-Bicyclo[3.3.0]octane-3,7-dione 14c (1.80 g, 13 mmol) was dissolved in 25 mL of concentrated hydrochloric acid in an ice-water bath, added with sodium azide (1.10 g, 16.90 mmol) in batches, then heated to room temperature and stirred for 12 hours. The reaction solution was added dropwise with 20% sodium hydroxide solution to adjust pH to 10 to 11, extracted with dichloromethane (50 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL×3), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (cis)-2,4,4a,5,7,7a-hexahydro-1H-cyclopenta[c]pyridine-3,6-dione 14d (3 g, yield: 100.0%) as a white solid.
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