1-[4-(Bromomethyl)phenyl]-1H-pyrrole → HCID 54243183, compound

HRID 1600575Notes

Reaction equation

HRID 1600575 reaction equation
[Li].C[Si]([NH-])(C)C.[CH3:7][O:8][C:9](=[O:25])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1.[N:26]1([C:31]2[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27]1>C1COCC1>[CH3:7][O:8][C:9](=[O:25])[C@:10]1([CH2:35][C:34]2[CH:33]=[CH:32][C:31]([N:26]3[CH:30]=[CH:29][CH:28]=[CH:27]3)=[CH:38][CH:37]=2)[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:24])[C:16]1[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=1

Participants

6

Reactant 4

HCID 27954561-[4-(Bromomethyl)phenyl]-1H-pyrroleHCID 3028194LithiumHCID 53627528(Trimethylsilyl)amideHCID 53972052HCID 53972052, compound

Product 1

HCID 54243183HCID 54243183, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a -78° C. solution of lithium bis(trimethylsilylamide (8 mL, 8 mmol) in THF is slowly added N-(3,5-dimethylbenzoyl)proline methyl ester (1.0 g, 3.8 mmol). After 20 minutes p-(1-pyrrolyl)-benzyl bromide (950 mg) in 5 mL of THF is added over a 5 minute period. The solution is warmed to room temperature, quenched with acetic acid and concentrated under reduced pressure. The residue is extracted with EtOAc. The organic layer is washed with NH4Cl (sat.), NaHCO3 solution, dried (MgSO4) and chromatographed on silica gel eluting with hexane/ethyl acetate (3:1) giving N-(3,5-dimethylbenzoyl)-2-[p-(1-pyrrolyl)-benzyl]-proline methyl ester.

Workup

  1. customTo a -78° C.
  2. customquenched with acetic acid
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue is extracted with EtOAc
  5. washThe organic layer is washed with NH4Cl (sat.), NaHCO3 solution
  6. dry with materialdried (MgSO4)
  7. customchromatographed on silica gel eluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-e809b965ce1c4adc8fd977300b80d450
Source dataset
uspto-grants-1999_11
Patent number
US05977075

Reaction notes

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