Water → Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (50.1 g) in N,N-dimethylacetamide (550 ml) was added sodium hydride (10.5 g) with stirring under ice-cooling, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, to the reaction mixture was added dropwise a solution of 4-fluoronitrobenzene (42.2 g) in N,N-dimethylacetamide (100 ml) with stirring at the same temperature, and the resulting mixture was furthermore stirred at room temperature overnight. After stirring, to the reaction mixture was added water and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (13:7) as the eluent to afford the title compound (75.1 g, yield: 93%) as a pale yellow solid.

1. temperaturecooling
2. stirringthe resulting mixture was stirred at the same temperature for 30 minutes
3. stirringwith stirring at the same temperature
4. stirringthe resulting mixture was furthermore stirred at room temperature overnight
5. stirringAfter stirring, to the reaction mixture
6. extractionthe resulting mixture was extracted with ethyl acetate
7. washThe extract was washed with a saturated aqueous sodium chloride solution
8. dry with materialdried over anhydrous magnesium sulfate
9. customevaporated in vacuo
10. customThe residue obtained
11. customwas purified by chromatography on a silica gel column

ORD record

ord-f06f7e416f8a4d0bae8ee5d5f2b3938e

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030138B2