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

HRID 750422노트

반응식

HRID 750422 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-0c3136aad15d41338df21b5a5c1e8c7a
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405065B2

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