Sulfuric Acid → N-[2-(1,6-dihydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)ethyl]propanamide

HRID 2389938ノート

反応式

HRID 2389938 の反応式
[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH2:11][C:10](=[CH:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[C:8]3=2)[O:3][CH2:2]1.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1.C(=O)([O-])O.[Na+]>[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH:11]=[C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[C:8]3=2)[O:3][CH2:2]1

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 66601781N-[2-(1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylidene)ethyl]propanamide

生成物 1

HCID 59179415N-[2-(1,6-dihydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)ethyl]propanamide収率 16%

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of N-[2-(1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylidene)ethyl]propanamide (612 mg, 2.37 mmol) in xylene (20 mL) was added sulfuric acid (693 μL, 12.9 mmol), and the mixture was heated under reflux for 22 hr. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate) to give the title compound (97.0 mg, yield 16%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 22 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate)

出典と根拠

ORDレコード
ord-335962c957164424817f4d5d3d3c19bc
出典データセット
uspto-grants-2012_09
特許番号
US08273761B2

反応ノート

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