Sodium Carbonate → HCID 9900678、化合物

HRID 983906ノート

反応式

HRID 983906 の反応式
[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

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 30165Iodide IonHCID 9815102HCID 9815102、化合物

生成物 1

HCID 9900678HCID 9900678、化合物収率 47%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-432645f26f064ca68a09be639b3da691
出典データセット
uspto-grants-2005_03
特許番号
US06867211B2

反応ノート

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