Sodium Hydroxide → 8-Benzyl-8-azabicyclo[3.2.1]octan-3-one oxime

HRID 1992044Notes

Reaction equation

HRID 1992044 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=O)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19].[OH-].[Na+]>C(O)C.O>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[N:18][OH:19])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 132767338-Benzyl-8-azabicyclo[3.2.1]octan-3-one oximeYield 82.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.85 g (22.56 mmol) of 8-benzyl-8-azabicyclo[3.2.1]octan-3-one was dissolved in 60 ml of ethanol. 3.13 g (45 mmol) hydroxylamine hydrochloride was then added followed by 1.8 g (45 mmol) of NaOH in 15 ml of water. The mixture was refluxed for 20 hrs and was cooled to ambient temperature. The solvent was removed in vaccuo. The residue was diluted with ethyl acetate and washed with water and the organic layer was dried over sodium sulfate. The solvent was removed to give 4.28 g of product as a light yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 20 hrs
  2. customThe solvent was removed in vaccuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-d20cd845f7024a7e9ff5c80b6d22a67c
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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