Iodine → 1-{[1-(4-Iodophenyl)cyclopropyl]carbonyl}pyrrolidine

HRID 230623Notes

Reaction equation

HRID 230623 reaction equation
[C:1]1([C:7]2([C:10]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[I:22](O)(=O)(=O)=O.II.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C.O>[I:22][C:4]1[CH:3]=[CH:2][C:1]([C:7]2([C:10]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])[CH2:8][CH2:9]2)=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 65185Metaperiodic acidHCID 656671Sodium PyrosulfiteHCID 57762795(1-Phenylcyclopropyl)(pyrrolidin-1-yl)methanone

Product 1

HCID 577628281-{[1-(4-Iodophenyl)cyclopropyl]carbonyl}pyrrolidineYield 531.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1-[(1-phenylcyclopropyl)carbonyl]pyrrolidine (0.75 g, 3.49 mmol) was dissolved in glacial acetic acid (14 ml) and treated successively with concentrated sulfuric acid (0.4 ml), water (1.5 ml), periodic acid (184 mg, 0.8 mmol), and iodine (379 mg, 1.49 mmol). This mixture was then stirred at 60° C. for 6 hours and then allowed to cool to room temperature. The reaction mixture was poured into a 10% aqueous solution of sodium metabisulfite and extracted into ethyl acetate. The organic layer was separated and dried over anhydrous sodium sulphate and evaporated under reduced pressure to give a yellow oil (1.45 g) which was added to a 20 g pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a yellow oil (0.62 g, 52%).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c03e32d4a4ff4b82b3b5d5621c5558b9
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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