Piperazine → HCID 68289207, compound

Temperature

0 °C

A mixture of 3-(4-methoxybenzyl)-6-(4-methoxyphenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione (0.86 g, 2.6 mmol), NaBH4 (0.296 g, 7.8 mmol) and BF3 etherate (1.0 mL, 7.8 mmol) in THF was heated under reflux overnight. After cooling to 0° C., a solution of piperazine (2 g) in H2O (20 mL) was added. The mixture was stirred at room temperature for 2 h, poured into H2O and extracted with EtOAc (3×). The combined organic extract was dried over MgSO4, filtered and then concentrated. The residue was purified by flash column chromatography with EtOAc in hexane (10%, 20%, then 30%) to give a white solid. To a suspension of the solid in THF (20 mL) and H2O (10 mL) was added piperazine (3 g). After heating the mixture under reflux overnight, it was poured into brine and extracted with EtOAc (3×). The combined organic extract was dried over MgSO4, filtered and concentrated to give the title compound as white solid (0.51 g, 65% yield). MS [M+H]+: 310.

1. temperaturewas heated
2. temperatureunder reflux overnight
3. extractionextracted with EtOAc (3×)
4. extractionThe combined organic extract
5. dry with materialwas dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by flash column chromatography with EtOAc in hexane (10%, 20%
9. custom30%) to give a white solid
10. temperatureAfter heating the mixture
11. temperatureunder reflux overnight
12. extractionextracted with EtOAc (3×)
13. extractionThe combined organic extract
14. dry with materialwas dried over MgSO4
15. filtrationfiltered
16. concentrationconcentrated

ORD record

ord-fe3971306f6b42cb9c09acb92504b37c

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2