Methanol → (S)-3-(4-bromophenyl)cyclopentanone oxime

HRID 2404368Notes

Reaction equation

HRID 2404368 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.CO.C([O-])(=O)C.[Na+].Cl.[NH2:22][OH:23]>CC(OC)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10](=[N:22][OH:23])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 25002103(S)-3-(4-Bromophenyl)cyclopentan-1-one

Product 1

HCID 86671372(S)-3-(4-bromophenyl)cyclopentanone oximeYield 95.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A slurry of (S)-3-(4-bromophenyl)cyclopentanone (prepared according to J. Org. Chem., 2009, 74, 929; 10.9 g, 45.5 mmol), MeOH (110 mL), sodium acetate (5.59 g, 68.2 mmol), and hydroxylamine hydrochloride (4.74 g, 68.2 mmol) was stirred at room temperature. After 10 minutes, LCMS showed complete reaction. Diluted with MTBE (300 mL) and washed with water (100 mL) and brine (50 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (gradient elution, 25-50% EtOAc/hexanes) to afford the title compound (11.0 g, 43.3 mmol, 95%). MS (DCI) m/z 254 (M+H)+.

Workup

  1. customreaction
  2. washwashed with water (100 mL) and brine (50 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (gradient elution, 25-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1b061fa03ab84f1db8c8abc4bdbe0663
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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