Sodium Carbonate → HCID 9900678, compound

HRID 983906Notes

Reaction equation

HRID 983906 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 9900678HCID 9900678, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

[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.

Workup

  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

Sources & evidence

ORD record
ord-432645f26f064ca68a09be639b3da691
Source dataset
uspto-grants-2005_03
Patent number
US06867211B2

Reaction notes

Loading…