Ethyl 4-oxo-1-piperidinecarboxylate → HCID 69266268, compound

To a stirred solution of 1-(2-bromophenyl)ethanol (step 1, 5.4 g, 25.1 mmol) in tetrahydrofuran (25 mL) was added dropwise a 1.59 M solution of butyllithium in tetrahydrofuran (33 mL, 51.5 mmol) at −78° C. for 20 min and the mixture was stirred for 2 h at the same temperature. To the mixture was added dropwise a solution of ethyl 4-oxopiperidine-1-carboxylate (4.73 g, 27.6 mmol) in tetrahydrofuran (10 mL) at −78° C. for 15 min. This resulting mixture was slowly warmed up to room temperature and stirred for 19 h at the same temperature. The reaction mixture was quenched by the addition of saturated ammonium chloride aqueous solution, and then the organic layer washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (150 g) eluting with hexane/ethyl acetate (2/1), then hexane/ethyl acetate (1/1) to afford 1.37 g (19%) of the title compound as a slight yellow syrup:

1. stirringstirred for 19 h at the same temperature
2. customThe reaction mixture was quenched by the addition of saturated ammonium chloride aqueous solution
3. washthe organic layer washed with brine
4. dry with materialdried over sodium sulfate
5. customevaporated
6. customThe residue was purified by column chromatography on silica gel (150 g)
7. washeluting with hexane/ethyl acetate (2/1)

ORD record

ord-4c009baefa234132806af6f8ed7c7f45

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354925B2