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Add 13.0 mL (75.0 mmol) of ethyldiisopropylamine to a solution of 2.0 g (7.5 mmol) of ethyl 2-bromo-2-fluoro-2-(3-oxocyclopentyl)acetate (Preparation 57) in DMF (8 mL), at 0° C., and stir the mixture overnight at room temperature. Add a solution of HCl 1N (20 mL), water (15 mL), and EtOAc (75 mL). Extract the organic layer, wash with saturated NaHCO3 (2×100 mL), water (2×100 mL), and brine (2×100 mL), dry over anhydrous MgSO4, filter and concentrate under reduced pressure. Purify the residue by column chromatography using EtOAc/hexane (1:4) as eluent to give the title compound (1.17 g, 84% yield) as a mixture trans:cis 5:1 of isomers as a colorless oil.

1. extractionExtract the organic layer
2. washwash with saturated NaHCO3 (2×100 mL), water (2×100 mL), and brine (2×100 mL)
3. dry with materialdry over anhydrous MgSO4
4. filtrationfilter
5. concentrationconcentrate under reduced pressure
6. customPurify the residue by column chromatography