Bromocyclopentane → HCID 60155353, compound

Temperature

60 °C

To a solution of compound (8) (0.50 g, 2.5 mmol) in dry DMF (5 mL), potassium carbonate (1.2 g, 8.8 mmol), and bromocyclopentane (0.32 g, 3.0 mmol) were added and stirred at 60° C. for 5 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate (300 mL) followed by washing with water and drying (over sodium sulfate). The solvent was distilled off, and the residue was dissolved in dichloromethane and washed with a 1 M-aqueous solution (30 mL) of sodium hydroxide. The organic layer was dried (over sodium sulfate) and distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution followed by conventional hydrolysis to give 0.56 g (84%) of compound (14) of interest as white solid.

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate was concentrated under reduced pressure
3. extractionThe residue was extracted with ethyl acetate (300 mL)
4. washby washing with water
5. dry with materialdrying (over sodium sulfate)
6. distillationThe solvent was distilled off
7. dissolutionthe residue was dissolved in dichloromethane
8. washwashed with a 1 M-aqueous solution (30 mL) of sodium hydroxide
9. dry with materialThe organic layer was dried (over sodium sulfate)
10. distillationdistilled off under reduced pressure
11. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution
12. customfollowed by conventional hydrolysis

ORD record

ord-67d32c544020407fa74a486de9d8c853

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221786B2