tert-butyl N-(2-oxocyclopentyl)carbamate → tert-Butyl N-[(2E)-2-{[5-(trifluoromethyl)pyridin-2-yl]methylidene}cyclopentyl]carbamate

HRID 1750533

반응식

HRID 1750533 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9]P(=O)(OCC)OCC)=[N:7][CH:8]=1.CC(C)([O-])C.[K+].O=[C:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]>C1COCC1>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[C:27]2/[CH:28]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH2:29][CH2:30][CH2:31]/2)=[N:7][CH:8]=1

참가 물질

5

반응물 3

HCID 357962tert-butyl N-(2-oxocyclopentyl)carbamateHCID 23665647Potassium tert-butoxideHCID 118320757Diethyl ((5-(trifluoromethyl)pyridin-2-yl)methyl)phosphonate

생성물 1

HCID 118308075tert-Butyl N-[(2E)-2-{[5-(trifluoromethyl)pyridin-2-yl]methylidene}cyclopentyl]carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To the suspension of diethyl ((5-(trifluoromethyl)pyridin-2-yl)methyl)phosphonate (2.0 g, 6.71 mmol) in THF (50 ml) at 0° C. was added potassium tert-butoxide (1.5 g, 13.42 mmol) and then stirred at room temperature for 30 minutes. To this was then added a solution of tert-butyl N-(2-oxocyclopentyl)carbamate (CAS number 477585-30-1; 1.62 g, 8.05 mmol) in THF (20 ml) and the resulting reaction was stirred at room temperature for 1 hour and then heated at reflux overnight. The reaction was quenched with water (50 ml) and extracted with ethyl acetate (3×100 ml). The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane) to afford the title compound.

후처리

  1. customthe resulting reaction
  2. stirringwas stirred at room temperature for 1 hour
  3. temperatureheated
  4. temperatureat reflux overnight
  5. customThe reaction was quenched with water (50 ml)
  6. extractionextracted with ethyl acetate (3×100 ml)
  7. washThe combined organics were washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane)

출처 및 근거

ORD 기록
ord-0960129e8ec84276924b2a52d92131e0
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156829B2

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