L-Methionine → 2-Methyl-2-phenyl-cyclopentanone

HRID 451101

Reaction equation

HRID 451101 reaction equation
[H-].[Na+].[C:3]1([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N[C@H:16](C(O)=O)CCSC>COCCOC>[CH3:16][C:9]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:13][CH2:12][CH2:11][C:10]1=[O:14]

Participants

5

Reactant 3

HCID 6137L-MethionineHCID 24758Sodium hydrideHCID 2901542-Phenylcyclopentanone

Product 1

HCID 3499412-Methyl-2-phenyl-cyclopentanoneYield 73.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a slurry of 60% NaH (125 mg, 3.12 mmol) in DME (3571 μL) at 0° C. was added 2-phenylcyclopentanone (500 mg, 3.12 mmol). After stirring for 1 h, Met (898 μL, 14.36 mmol) was added, and the solution heated to reflux for 2 h. The reaction was poured onto ice and extracted 3 times into Et20. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Applied to Silica gel and eluted with an EtOAc/Hex gradient to afford 2-methyl-2-phenylcyclopentanone (401.7 mg, 2.305 mmol, 73.9% yield). LC-MS (M+H)+=175.1. 1H NMR (500 MHz, CDCl3) δ ppm 7.29-7.37 (4H, m), 7.20-7.24 (1H, m), 2.54 (1H, dt, J=12.51, 6.26 Hz), 2.34 (2H, t, J=7.63 Hz), 1.82-2.05 (3H, m), 1.38 (3H, s).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 2 h
  3. additionThe reaction was poured onto ice
  4. extractionextracted 3 times into Et20
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washApplied to Silica gel and eluted with an EtOAc/Hex gradient

Sources & evidence

ORD record
ord-e4f023037c024b8398a7f56a2ff8b3f7
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Linked notes

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