Methanol → 4-(3-dimethylaminopropyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 24332Notes

Reaction equation

HRID 24332 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][C:13](=O)[N:14]([CH3:16])[CH3:15])=[CH:9][NH:8][C:7]=1[CH3:18])=[O:5])[CH3:2].B.O1CCCC1.CO>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[CH:9][NH:8][C:7]=1[CH3:18])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 54214711HCID 54214711, compound

Product 1

HCID 545595184-(3-dimethylaminopropyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a heterogeneous mixture of 4-(2-dimethylcarbamoyl-ethyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (1.01 g, 4 mmol) in THF (9 mL) was added dropwise 8 mL of borane-tetrahydrofuran complex (1M in THF). The mixture was refluxed overnight. Then 9.0 mL of MeOH was added slowly to the reaction and refluxing was continued for another 2 hr. The reaction mixture was cooled, quenched with 1N HCl and extracted with EtOAc. The aqueous layer was basified with aqueous KOH and extracted with EtOAc. The EtOAc extract was washed with brine, dried and concentrated to give 616 mg (65%) of 4-(3-dimethylaminopropyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester as a faint orange oil.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturerefluxing
  3. temperatureThe reaction mixture was cooled
  4. customquenched with 1N HCl
  5. extractionextracted with EtOAc
  6. extractionextracted with EtOAc
  7. extractionThe EtOAc extract
  8. washwas washed with brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-81737b740b954e72894a0e43971d7c35
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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