Sulfuric Acid → 3-(Pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine

HRID 2388698노트

반응식

HRID 2388698 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:11]3[CH2:12][N:13](C(=O)C)[CH2:14][CH2:15][C:10]3(N3CCCC3)[O:9][N:8]=2)=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[OH-].[Na+]>O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:11]3[CH2:12][NH:13][CH2:14][CH2:15][C:10]=3[O:9][N:8]=2)=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 686439771-(3-(Pyridin-4-yl)-7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridin-5(6H)-yl)ethanone

생성물 1

HCID 579486603-(Pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

1-(3-(Pyridin-4-yl)-7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridin-5(6H)-yl)ethanone (0.63 g, 2 mmol) was initially introduced into water (14 ml) and sulfuric acid (95%, 14 ml) was added. The reaction mixture was refluxed for 5 hours, cooled with an ice bath, neutralized with sodium hydroxide solution (5 mol/l) and concentrated in vacuo. Ethyl acetate (10 ml) was added to the residue and the suspension was stirred at room temperature for 30 minutes. The precipitate was filtered out with suction and the mother liquor was extracted with ethyl acetate (4×20 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The yield was 0.34 g (84%). [The regiochemistry was assigned in analogy to AM1-AM4.]

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 5 hours
  3. temperaturecooled with an ice bath
  4. concentrationconcentrated in vacuo
  5. additionEthyl acetate (10 ml) was added to the residue
  6. filtrationThe precipitate was filtered out with suction
  7. extractionthe mother liquor was extracted with ethyl acetate (4×20 ml)
  8. dry with materialThe combined organic phases were dried (MgSO4)
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4bc3b9f4d92041139964f38864905800
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

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