Acetic Anhydride → 3-Methyl-2,6-piperidinedione

HRID 1260405ノート

反応式

HRID 1260405 の反応式
C(OC(=O)C)(=O)C.[CH3:8][CH:9]([CH2:13][CH2:14][C:15]([OH:17])=O)[C:10](O)=[O:11].[NH4+:18].[OH-]>>[CH3:8][CH:9]1[CH2:13][CH2:14][C:15](=[O:17])[NH:18][C:10]1=[O:11]

参加物

4

反応物 3

HCID 7918Acetic AnhydrideHCID 120462-Methylglutaric AcidHCID 14923Ammonium Hydroxide

生成物 1

HCID 346293-Methyl-2,6-piperidinedione収率 78.9%

反応条件

温度
60 °C

実験手順

Acetic anhydride was added to commercially available 2-methylglutaric acid (1 g, 6.8 mmol) at room temperature, and the mixture was stirred at 60° C. for 8 hours under reflux. After completion of the reaction was confirmed by TLC, the remaining acetic anhydride was removed under reduced pressure. The concentrated compound was dissolved in tetrahydrofuran and an ammonia aqueous solution (1.7 mL, 14.6 mmol) was slowly added thereto at 0° C., followed by stirring for 8 hours at room temperature. After the reaction was complete, the remaining ammonia aqueous solution was removed under reduced pressure and an acetic anhydride was added, followed by reflux at 60° C. for 8 hours. The residual acetic anhydride was removed under reduced pressure. The concentrate was purified by column chromatography (ethyl acetate:hexane=1:1) to afford 682 mg (yield: 78%) of the title compound.

後処理

  1. temperatureunder reflux
  2. customthe remaining acetic anhydride was removed under reduced pressure
  3. dissolutionThe concentrated compound was dissolved in tetrahydrofuran
  4. customat 0° C.
  5. stirringby stirring for 8 hours at room temperature
  6. customthe remaining ammonia aqueous solution was removed under reduced pressure
  7. additionan acetic anhydride was added
  8. temperatureby reflux at 60° C. for 8 hours
  9. customThe residual acetic anhydride was removed under reduced pressure
  10. customThe concentrate was purified by column chromatography (ethyl acetate:hexane=1:1)

出典と根拠

ORDレコード
ord-31d97895ca8748928ba7fa5a1b3cf919
出典データセット
uspto-grants-2013_06
特許番号
US08470836B2

反応ノート

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