Imidazole → HCID 57301964, compound

HRID 1167476Notes

Reaction equation

HRID 1167476 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:9]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58720906(3R)-1-(2-Fluoro-4-nitrophenyl)pyrrolidin-3-ol

Product 1

HCID 57301964HCID 57301964, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-4-((3R)-3-hydroxy-1-pyrrolidinyl)nitrobenzene (35.8 g, 0.158 M) was dissolved in DMF (200 ml), and treated with imidazole (21.6 g, 0.318 M) and t-butyldimethylsilyl chloride (35.7 g, 0.239 M) and stirred for 18 hours at ambient temperature under nitrogen. Solvent was evaporated, and the residue treated with EtOAc (300 ml) and water (200 ml). The organic layer was washed with water (150 ml) and dried (magnesium sulfate). Evaporation gave the desired product (54 g), of sufficient quality for use without purification.

Workup

  1. customSolvent was evaporated
  2. additionthe residue treated with EtOAc (300 ml) and water (200 ml)
  3. washThe organic layer was washed with water (150 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customEvaporation

Sources & evidence

ORD record
ord-412ea8a865bf4ce39c9c04b0dff25056
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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