Sodium Carbonate → HCID 9900678, 화합물

HRID 983906노트

반응식

HRID 983906 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([CH2:12][CH2:13][CH2:14]3)=[C:10]([CH2:16]O)[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.I.[I-].C([O-])([O-])=O.[Na+].[Na+]>O.C(OCC)(=O)C.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:15]3[C:11](=[C:10]([CH3:16])[C:9]=2[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH2:12][CH2:13][CH2:14]3)=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 30165Iodide IonHCID 9815102HCID 9815102, 화합물

생성물 1

HCID 9900678HCID 9900678, 화합물수율 47%

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

[3-(4-Fluorophenyl)-2-(4-pyridyl)-6,7-dihydro-5H-pyrrolizin-1-yl]methanol (3.08 g, 10 mmol) is heated with hydriodic acid (57%, 18 ml, 134 mmol HI) in an oil bath at 120° C. (reflux). The initially undissolved substance has dispersed in the batch after 45 min, and starting material (rf=0.05) is no longer detectable (product rf=0.9, iodide rf=0.6) by tlc (ether, Al2O3). After cooling (1 h), the solution is diluted with 50 ml of water and covered with a layer of 100 ml of ethyl acetate. The water phase is carefully neutralized with sat. Na2CO3 soln (30 ml) and the phases are separated. The water phase again extracted with ethyl acetate (50 ml), the combined ethyl acetate extracts decolorized using sodium thiosulfate solution (Na2S2O3, 2% strength, 40 ml) and, after washing again with water (50 ml), dried over Na2SO4 sicc. After evaporating the solvent in vacuo, 2.28 g of residue remain, which solidifies from CH2Cl2/ethyl acetate to give a resinous mass. The substance is purified by CC (Al2O3/ether) and the substance obtained from the fractions by evaporating the solvent (fractions 1-17, 1.74 g) is crystallized from diisopropyl ether. 1.37 g of pure compound are obtained.

후처리

  1. temperature(reflux)
  2. additionThe initially undissolved substance has dispersed in the batch after 45 min
  3. temperatureAfter cooling (1 h)
  4. customthe phases are separated
  5. extractionThe water phase again extracted with ethyl acetate (50 ml)
  6. washafter washing again with water (50 ml)
  7. dry with materialdried over Na2SO4 sicc
  8. customAfter evaporating the solvent in vacuo, 2.28 g of residue
  9. customto give a resinous mass
  10. customThe substance is purified by CC (Al2O3/ether)
  11. customthe substance obtained from the fractions
  12. customby evaporating the solvent (fractions 1-17, 1.74 g)
  13. customis crystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-432645f26f064ca68a09be639b3da691
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867211B2

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