Pyridine → (1R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-one O-methyl oxime

HRID 75059Notes

Reaction equation

HRID 75059 reaction equation
[CH3:1][C:2]1([CH3:10])[C@@H:7]2[CH2:8][C@H:3]1[CH2:4][CH2:5][C:6]2=O.Cl.[CH3:12][O:13][NH2:14].N1C=CC=CC=1>C(O)C>[CH3:12][O:13][N:14]=[C:6]1[CH2:5][CH2:4][C@H:3]2[CH2:8][C@@H:7]1[C:2]2([CH3:10])[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 157139Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-, (1S,5R)-HCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 86667458(1R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-one O-methyl oximeYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1S,5R)-6,6-dimethylnorpinan-2-one (3.09 g, 22.35 mmol) in ethanol (70 mL) was added O-methylhydroxylamine hydrochloride (2.05 g, 24.59 mmol) and pyridine (1.29 mL, 15.92 mmol). Heated reaction mixture to 80° C. for 4 hours. Removed solvent under reduced pressure. Diluted residue with 1N HCl and extracted twice with ether. The combined organic phases were washed with aqueous saturated NaHCO3, dried (MgSO4), filtered, concentrated in vacuo to afford 3.36 g of a colorless oil (mixture of oxime isomers) that was used without further purification.

Workup

  1. temperatureHeated
  2. customreaction mixture to 80° C. for 4 hours
  3. extractionDiluted residue with 1N HCl and extracted twice with ether
  4. washThe combined organic phases were washed with aqueous saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fe98efbc4fa4caf925e9c6cb89d86c9
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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