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

HRID 451101

반응식

HRID 451101 반응식
[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]

참가 물질

5

반응물 3

HCID 6137L-MethionineHCID 24758Sodium hydrideHCID 2901542-Phenylcyclopentanone

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e4f023037c024b8398a7f56a2ff8b3f7
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486952B2

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