HCID 18542632, compound → HCID 18542720, compound

Temperature

40 °C

A solution of dimethyl 2-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-nitroisophthalate (10.7 g) in concentrated hydrochloric acid (100 ml) was stirred at 80° C. for 10 hours. The reaction mixture was concentrated in vacuo. To the residue was added hexane to afford a white solid which was collected by filtration. To a solution of the solid in a mixture of water (50 ml) and acetone (50 ml) were added sodium hydrogencarbonate (4.6 g) and di-t-butyl dicarbonate (5.9 g) at room temperature. The resulting mixture was stirred at 40° C. for 1 hour. The reaction mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated in vacuo. To the residue was added hexane and the mixture was filtered to give the desired compound (4.1 g, yield 40%) as a pale yellow solid.

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionTo the residue was added hexane
3. customto afford a white solid which
4. filtrationwas collected by filtration
5. additionTo a solution of the solid in a mixture of water (50 ml) and acetone (50 ml)
6. additionwere added sodium hydrogencarbonate (4.6 g) and di-t-butyl dicarbonate (5.9 g) at room temperature
7. extractionThe reaction mixture was extracted with ethyl acetate
8. washThe extract was washed with brine
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationthe filtrate was concentrated in vacuo
12. additionTo the residue was added hexane
13. filtrationthe mixture was filtered

ORD record

ord-7227a9e683c1404aac6c9c450ebf98ab

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555556B1