tert-butyl N-(2-oxocyclopentyl)carbamate → tert-Butyl N-[(2E)-2-{[5-(trifluoromethyl)pyridin-2-yl]methylidene}cyclopentyl]carbamate

To the suspension of diethyl ((5-(trifluoromethyl)pyridin-2-yl)methyl)phosphonate (2.0 g, 6.71 mmol) in THF (50 ml) at 0° C. was added potassium tert-butoxide (1.5 g, 13.42 mmol) and then stirred at room temperature for 30 minutes. To this was then added a solution of tert-butyl N-(2-oxocyclopentyl)carbamate (CAS number 477585-30-1; 1.62 g, 8.05 mmol) in THF (20 ml) and the resulting reaction was stirred at room temperature for 1 hour and then heated at reflux overnight. The reaction was quenched with water (50 ml) and extracted with ethyl acetate (3×100 ml). The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane) to afford the title compound.

1. customthe resulting reaction
2. stirringwas stirred at room temperature for 1 hour
3. temperatureheated
4. temperatureat reflux overnight
5. customThe reaction was quenched with water (50 ml)
6. extractionextracted with ethyl acetate (3×100 ml)
7. washThe combined organics were washed with brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated in vacuo
10. customThe resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane)

ORD record

ord-0960129e8ec84276924b2a52d92131e0

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156829B2