Hydrochloric Acid → Ethyl(1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate

HRID 2222736Notes

Reaction equation

HRID 2222736 reaction equation
C(N(C(C)C)C(C)C)C.Br[C:11]([F:23])([CH:17]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl.O>CN(C=O)C.CCOC(C)=O>[F:23][C:11]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:18]2[CH:17]1[CH2:21][CH2:20][C:19]2=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 81531DiisopropylethylamineHCID 11380123HCID 11380123, compound

Product 1

HCID 9964278Ethyl(1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-55d41211b7184384a4e6a670a6029d7b
Source dataset
uspto-grants-2008_05
Patent number
US07371872B2

Reaction notes

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