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 1582320ノート

反応式

HRID 1582320 の反応式
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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 2855718-Crown-6触媒HCID 12110454(1S,2S)-1-(bromomethyl)-2-methylcyclopropane触媒HCID 23665647Potassium tert-butoxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-04df401df7d1476da37b0759a4dc8d30
出典データセット
uspto-grants-2004_05
特許番号
US06734181B2

反応ノート

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