Hydrochloric Acid → 2-Aza-2-benzyl-4-oximino-3-oxo-bicyclo[3,2,1]octane

HRID 133217Notes

Reaction equation

HRID 133217 reaction equation
[CH2:1]([CH:8]1[C:14](=[O:15])[CH2:13][CH:12]2[CH2:16][CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CC([O-])(C)C.[K+].C1COCC1.[N:28](OCCC(C)C)=[O:29].Cl>C1COCC1>[CH2:1]([CH:8]1[C:14](=[O:15])[C:13](=[N:28][OH:29])[CH:12]2[CH2:16][CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 223126692-Aza-2-benzyl-3-oxo-bicyclo[3,2,1]octaneHCID 66863523KOtBu THF

Product 1

HCID 865849682-Aza-2-benzyl-4-oximino-3-oxo-bicyclo[3,2,1]octaneYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aza-2-benzyl-3-oxobicyclo[3.2.1]octane in THF was added 2.5 eq. of 1M t-BuOK/THF (Aldrich) and the resulting mixture was stirred for 30 minutes. Isoamyl nitrite (1.5 eq.) was then added dropwise and the reaction mixture was stirred overnight. To the reaction mixture was added 3N HCl and this mixture was extracted with ethyl acetate and the organic extracts washed with water, dried, and concentrated under reduced pressure. The residue was triturated with ether/hexanes, the solvents decanted and the residue dried under reduced pressure to afford 2-aza-2-benzyl-4-oximino-3-oxobicyclo[3.2.1]octane as a tan liquid (41% yield). This procedure is further described in Y. Kim, Tetrahedron Lett. 30(21), 2833-2636 (1989).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. extractionthis mixture was extracted with ethyl acetate
  3. washthe organic extracts washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with ether/hexanes
  7. customthe solvents decanted
  8. customthe residue dried under reduced pressure

Sources & evidence

ORD record
ord-4301332baf2d47a185fe6dd275a7a5d0
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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