Iodine → 1-[2-(4-Iodo-phenyl)-ethyl]pyrrolidin-2-one

HRID 521743Notes

Reaction equation

HRID 521743 reaction equation
[CH2:1]([N:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(=O)(=O)(O)O.II.[I:22](O)(=O)(=O)=O>C(O)(=O)C.O>[I:22][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][CH2:1][N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 65185Metaperiodic acidHCID 7469811-(2-Phenylethyl)pyrrolidin-2-one

Product 1

HCID 897931171-[2-(4-Iodo-phenyl)-ethyl]pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of HJC-1-53 (500 mg, 2.6 mmol), water (1 mL), 95% sulfuric acid (285 mg, 2.9 mmol) and acetic acid (8 mL) was added iodine (335 mg, 1.3 mmol) and periodic acid (H5IO6, 150 mg, 0.7 mmol) at rt. The reaction mixture was warmed to 60° C. for 3 h. After cooling down to rt, the solution was extracted with EtOAc (80 mL) and H2O (20 mL), and washed with 10% NaHSO3 (20 mL), followed by 10% NaHCO3 (40 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/2) to obtain HJC-1-60 (130 mg, 16%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.60 (d, 1H, J=7.8 Hz), 7.26-7.30 (m, 1H), 7.19-7.21 (m, 1H), 6.96 (d, 1H, J=9.0 Hz), 3.48-3.53 (m, 2H), 3.23-3.26 (m, 2H), 2.83 (t, 1H, J=7.8 Hz), 2.78 (t, 1H, J=7.8 Hz), 2.32-2.36 (m, 2H), 1.91-1.97 (m, 2H).

Workup

  1. temperatureAfter cooling down to rt
  2. extractionthe solution was extracted with EtOAc (80 mL) and H2O (20 mL)
  3. washwashed with 10% NaHSO3 (20 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil residue
  10. customThis residue was purified with silica gel column (Hexane/EtOAc=1/2)
  11. customto obtain HJC-1-60 (130 mg, 16%) as a pale yellow oil

Sources & evidence

ORD record
ord-dddd7f2965a44150aec9c78470fe2ea7
Source dataset
uspto-grants-2016_05
Patent number
US09328125B2

Reaction notes

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