Iodine → (6R*,9aS*)-6-(3-fluorophenyl)-3-iodooctahydroquinolizin-4-one

HRID 553906Notes

Reaction equation

HRID 553906 reaction equation
I[Si](C)(C)C.[F:6][C:7]1[CH:8]=[C:9]([C@H:13]2[CH2:22][CH2:21][CH2:20][C@@H:19]3[N:14]2[C:15](=[O:23])[CH2:16][CH2:17][CH2:18]3)[CH:10]=[CH:11][CH:12]=1.CN(C)CCN(C)C.[I:32]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[C:9]([C@H:13]2[CH2:22][CH2:21][CH2:20][C@@H:19]3[N:14]2[C:15](=[O:23])[CH:16]([I:32])[CH2:17][CH2:18]3)[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 5

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 69071146(6R*,9aS*)-6-(3-fluorophenyl)octahydroquinolizin-4-one

Product 1

HCID 69075941(6R*,9aS*)-6-(3-fluorophenyl)-3-iodooctahydroquinolizin-4-oneYield 103.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodotrimethylsilane (0.34 mL) was added to a solution of (6R*,9aS*)-6-(3-fluorophenyl) octahydroquinolizin-4-one (383 mg) and N,N,N′,N′-tetramethylethylenediamine (0.82 mL) in methylene chloride (15 mL) under ice-cooling in a nitrogen atmosphere, and the reaction solution was stirred under ice-cooling for 30 minutes. Iodine (590 mg) was added to the reaction solution under ice-cooling, and the reaction solution was stirred under ice-cooling for one hour. Ethyl acetate and a saturated sodium thiosulfate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 597 mg of the title compound. The property value of the compound is as follows.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. temperaturecooling for 30 minutes
  3. temperaturecooling
  4. stirringthe reaction solution was stirred under ice-
  5. temperaturecooling for one hour
  6. customthe organic layer was separated
  7. washThe resulting organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad84cbae4c9a420282e4f6bafe4bb616
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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