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

HRID 2417312Notes

Reaction equation

HRID 2417312 reaction equation
Br[C:2]([F:14])([CH:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1CCN2C(=NCCC2)CC1.Cl>CN(C)C=O>[F:14][C:2]1([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:9]2[CH:8]1[CH2:12][CH2:11][C:10]2=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11380123HCID 11380123, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2SR)ethyl 2-bromo-2-fluoro-2-[(1RS)-3-oxocyclopentyl]acetate in an amount of 1.00 g was dissolved in 5.0 mL of N,N-dimethylformamide, and 0.84 g of 1,8-diazabicyclo[5.4.0]-7-undecene was added thereto, followed by stirring for 5 hours at room temperature. The reaction mixture was poured into 1M hydrochloric acid, followed by extractions with ethyl acetate twice. The organic layers were combined, and the combined organic layer was subsequently dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (produced by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=8:1), thereby yielding 0.68 g of (1RS,5RS,6RS)ethyl 6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate.

Workup

  1. extractionfollowed by extractions with ethyl acetate twice
  2. dry with materialthe combined organic layer was subsequently dried over anhydrous sodium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel: Wako gel C200 (produced by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=8:1)

Sources & evidence

ORD record
ord-45b5aec065b8458183c1c7f5e3d9d083
Source dataset
uspto-grants-2004_11
Patent number
US06825375B2

Reaction notes

Loading…