HCID 68413366, compound → HCID 68412786, compound

HRID 220233Notes

Reaction equation

HRID 220233 reaction equation
O[C:2]1([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH2:7][CH:6]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5]2=[O:10]>C1COCC1>[S:12]1[CH:13]=[CH:14][N:15]=[C:11]1[C:2]1[CH:3]2[CH2:9][CH2:8][CH:6]([CH:7]=1)[C:5](=[O:10])[CH2:4]2

Participants

3

Reactant 1

HCID 68413366HCID 68413366, compound

Product 1

HCID 68412786HCID 68412786, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

806 mg of 5-hydroxy-5-thiazol-2-yl-bicyclo[2.2.2]octan-2-one were dissolved in THF (7.2 mL) and 2.58 g of the Burgess'reagent was added portionwise at 0° C. The ice bath was removed and the reaction mixture was stirred at rt for 4 h, then quenched with cold water and extracted with DCM. The organic phase was washed with water and brine, dried over anh. Na2SO4, filtered and concentrated in vacuo. The crude material was purified by CC using EtOAc/heptane (1/2) as eluant to yield 412 mg of rac-(1R*,4R*)-5-thiazol-2-yl-bicyclo[2.2.2]oct-5-en-2-one as a yellowish oil.

Workup

  1. addition2.58 g of the Burgess'reagent was added portionwise at 0° C
  2. customThe ice bath was removed
  3. customquenched with cold water
  4. extractionextracted with DCM
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anh. Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by CC

Sources & evidence

ORD record
ord-bee83d07e87d45b0a7e05afa97645ab4
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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