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Acetic Anhydride → 2-Acetylhexahydrocyclopenta[c]pyrrol-5(1H)-one

HRID 1925081
ノート
印刷プレビュー

反応式

HRID 1925081 の反応式
[CH2:1]1[CH:5]2[CH2:6][C:7](=[O:9])[CH2:8][CH:4]2[CH2:3][NH:2]1.[C:10](OC(=O)C)(=[O:12])[CH3:11].C(N(CC)CC)C>C(#N)C>[C:10]([N:2]1[CH2:3][CH:4]2[CH2:8][C:7](=[O:9])[CH2:6][CH:5]2[CH2:1]1)(=[O:12])[CH3:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 46911901Hexahydrocyclopenta(c)pyrrol-5(1H)-one

生成物 1

HCID 109974182-Acetylhexahydrocyclopenta[c]pyrrol-5(1H)-one収率 72%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Hexahydro-cyclopenta[c]pyrrol-5-one triflutate 1f (717 mg, 3 mmol) was dissolved in 20 mL of acetonitrile, and acetic anhydride (0.42 mL, 4.5 mmol) and triethylamine (0.98 mL, 9 mmol) were then added to the solution in an ice-water bath. Upon completion of the addition, the reaction mixture was then stirred overnight in an ice-water bath. The solvent was evaporated, and water (50 mL) was then added to the residue. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic extracts were washed with 50 mL of saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 2-acetyl-hexahydro-cyclopenta[c]pyrrol-5-one 5a (0.36 g, yield 72%) as a colorless oil.

後処理

  1. additionUpon completion of the addition
  2. customThe solvent was evaporated
  3. additionwater (50 mL) was then added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (50 mL×3)
  5. washThe combined organic extracts were washed with 50 mL of saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-bad541be82e542d9aacba6855f0114a6
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178575B2

反応ノート

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