Sodium Hydroxide → rac-(4aR,7aR)-octahydro-1H-cyclopenta[c]pyridine-3,6-dione

(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.

1. extractionextracted with dichloromethane (50 mL×3)
2. washThe combined organic phase was washed with saturated sodium chloride solution (50 mL×3)
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-dc5cdccc87b94ccc9e0535a8638b70f5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2