Hexane → HCID 18542573, compound

Temperature

40 °C

A solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-methoxycarbonyl-5-methylnitrobenzene (4.0 g) in concentrated hydrochloric acid (40 ml) was stirred at 75° C. for 7 hours. The reaction mixture was concentrated in vacuo. To a solution of the residual colorless solid in a mixture of water (20 ml) and acetone (20 ml) were added sodium hydrogencarbonate (1.9 g) and di-t-butyl dicarbonate (2.7 g) in an ice bath. The resulting mixture was stirred at 40° C. for 2 hours. The reaction mixture was extracted with ethyl acetate. The extractant was washed with 0.5M hydrochloric acid, water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to afford a pale yellow solid. To the solid was added hexane and the mixture was filtered to give the desired compound (3.6 g, yield 79%) as a pale yellow solid.

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionTo a solution of the residual colorless solid in a mixture of water (20 ml) and acetone (20 ml)
3. additionwere added sodium hydrogencarbonate (1.9 g) and di-t-butyl dicarbonate (2.7 g) in an ice bath
4. extractionThe reaction mixture was extracted with ethyl acetate
5. washThe extractant was washed with 0.5M hydrochloric acid, water and brine
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customto afford a pale yellow solid
10. filtrationthe mixture was filtered

ORD record

ord-47c8d9ff77354be7bf2542f84cbc9928

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555556B1