Methyl iodide → (+/-)-(5S,7aR)-7-(2,5-Difluorophenyl)-2-methyl-5-phenyl-1,2,5,7a-tetrahydro-3H-pyrrolo[1,2-c]imidazol-3-one

HRID 32859Notes

Reaction equation

HRID 32859 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:16]2[N:12]([C:13](=[O:17])[NH:14][CH2:15]2)[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1.[H-].[Na+].I[CH3:27]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[C@H:16]2[N:12]([C:13](=[O:17])[N:14]([CH3:27])[CH2:15]2)[C@H:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11197726(+/-)-7-(2,5-Difluorophenyl)-5-phenyl-1,2,5,7a-tetrahydro-3H-pyrrolo[1,2-c]imidazol-3-one

Product 1

HCID 11404613(+/-)-(5S,7aR)-7-(2,5-Difluorophenyl)-2-methyl-5-phenyl-1,2,5,7a-tetrahydro-3H-pyrrolo[1,2-c]imidazol-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-4a (0.02 g, 0.06 mmol), sodium hydride (5 mg), and iodomethane (0.004 mL, 0.03 mmol) in THF (1.0 mL) was stirred at rt for 1 h. The reaction was quenched with water (2.0 mL) and extracted with EtOAc (20 mL). The organic solution was washed with brine, dried over MgSO4, filtered, and concentrated. The remaining oil was dissolved in CH3CN (0.5 mL) and purified on a Gilson automated system affixed with a YMC J'sphere H80 20×50 mm column (eluting with 5-95% CH3CN +0.1% TFA in water +0.1% TFA over 10 min) to afford pure 2A-1a.

Workup

  1. customThe reaction was quenched with water (2.0 mL)
  2. extractionextracted with EtOAc (20 mL)
  3. washThe organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe remaining oil was dissolved in CH3CN (0.5 mL)
  8. custompurified on a Gilson automated system
  9. washaffixed with a YMC J'sphere H80 20×50 mm column (eluting with 5-95% CH3CN +0.1% TFA in water +0.1% TFA over 10 min)

Sources & evidence

ORD record
ord-d26569c16d17482dafb2a153f0509410
Source dataset
uspto-grants-2008_09
Patent number
US07427637B2

Reaction notes

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