Water → (+/-)-2-Propionyl-2-azabicyclo[2.2.1]hept-5-en-3-one

HRID 840515ノート

反応式

HRID 840515 の反応式
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.N1C=CC=CC=1.[C:15](Cl)(=[O:18])[CH2:16][CH3:17].O>C(#N)C>[C:15]([N:2]1[C:3](=[O:8])[CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:18])[CH2:16][CH3:17]

参加物

6

反応物 4

HCID 962WaterHCID 1049PyridineHCID 62324Propionyl chlorideHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-one

生成物 1

HCID 22673281(+/-)-2-Propionyl-2-azabicyclo[2.2.1]hept-5-en-3-one収率 81.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

47 g of (±)-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in acetonitrile (325 ml) and pyridine (41 ml) under nitrogen. At 12° C., 43.9 g of propionyl chloride were added dropwise over the course of 1 h. The reaction was then stirred at room temperature for 5 h. 145 ml of water were added to the mixture, and the acetonitrile was evaporated off in vacuo. The aqueous phase was extracted 3 times with 115 ml of ethyl acetate. The combined organic phases were washed with 1N HCl (140 ml), saturated NaHCO3 (40 ml) and NaCl (40 ml) solutions, dried with sodium sulphate and completely evaporated. The residue was purified by distillation. 55.8 g of title compound were obtained and solidified on leaving to stand. The yield was 81.6%.

後処理

  1. customthe acetonitrile was evaporated off in vacuo
  2. extractionThe aqueous phase was extracted 3 times with 115 ml of ethyl acetate
  3. washThe combined organic phases were washed with 1N HCl (140 ml), saturated NaHCO3 (40 ml) and NaCl (40 ml) solutions
  4. dry with materialdried with sodium sulphate
  5. customcompletely evaporated
  6. distillationThe residue was purified by distillation

出典と根拠

ORDレコード
ord-91d9f69eba51484f8ee54c0243877d96
出典データセット
uspto-grants-2002_04
特許番号
US06368850B1

反応ノート

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