Iodine → HCID 69077078, compound

HRID 553875Notes

Reaction equation

HRID 553875 reaction equation
I[Si](C)(C)C.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:21][CH2:20][CH2:19][C@@H:18]3[N:14]2[C:15](=[O:22])[CH2:16][CH2:17]3)=[CH:9][CH:8]=1.CN(C)CCN(C)C.[I:31]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:21][CH2:20][CH2:19][C@H:18]3[N:14]2[C:15](=[O:22])[CH:16]([I:31])[CH2:17]3)=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 69077797HCID 69077797, compound

Product 1

HCID 69077078HCID 69077078, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Iodotrimethylsilane (0.08 mL) was added to a solution of (5R*,8aS*)-5-(4-fluorophenyl)hexahydroindolizin-3-one (87 mg) and N,N,N′,N′-tetramethylethylenediamine (0.2 mL) in methylene chloride (5 mL) at 0° C., and the reaction solution was stirred at 0° C. for 20 minutes. Iodine (142 mg) was added to the reaction solution, which was then stirred at 0° C. for 40 minutes. 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 120 mg of the title compound. The property value of the compound is as follows.

Workup

  1. stirringwas then stirred at 0° C. for 40 minutes
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-718b8d8d1de148bb94236bd81ee73eb1
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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