Methyl 3-formyl-4,5-dimethyl-1H-pyrrole-2-carboxylate → Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

HRID 1582320노트

반응식

HRID 1582320 반응식
CC(C)([O-])C.[K+].[CH:7]([C:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[NH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17])=[O:8].[CH3:20][C@H:21]1[CH2:23][C@@H:22]1[CH2:24]Br>O1CCCC1.C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].C[C@H]1C[C@@H]1CBr>[CH:7]([C:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]([CH2:20][C@H:21]2[CH2:23][C@@H:22]2[CH3:24])[C:10]=1[C:16]([O:18][CH3:19])=[O:17])=[O:8]

참가 물질

8

반응물 3

HCID 10773740Methyl 3-formyl-4,5-dimethyl-1H-pyrrole-2-carboxylateHCID 12110454(1S,2S)-1-(bromomethyl)-2-methylcyclopropaneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 12110455Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate수율 103.9%

시약·촉매·용매 4

HCID 2855718-Crown-6촉매HCID 12110454(1S,2S)-1-(bromomethyl)-2-methylcyclopropane촉매HCID 23665647Potassium tert-butoxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

Potassium tert-butoxide (3.49 g, 35.1 mmol) was added to a solution of methyl 3-formyl-4,5-dimethylpyrrole-2-carboxylate (5.79 g, 31.9 mmol) and 18-crown-6 (0.41 g, 1.55 mmol) in tetrahydrofuran (130 ml) and the mixture was stirred at room temperature for 1 hour. After dropwise addition over 30 minutes of (1S,2S)-2-methylcyclopropylmethyl bromide (5.71 g, 38.3 mmol) to the reaction mixture at 50° C., the mixture was heated under reflux for 3 hours. Potassium tert-butoxide (0.36 g, 3.22 mmol) and (1S,2S)-2-methylcyclopropylmethyl bromide (0.48 g, 3.21 mmol) were further added to the mixture and this mixture was heated for 1 hour. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to afford the desired compound (8.26 g, 100%) as a pale brown oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethis mixture was heated for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  7. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-04df401df7d1476da37b0759a4dc8d30
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734181B2

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