Dimethylamine → Ethyl 4-[(dimethylamino)methyl]-1H-pyrrole-2-carboxylate

HRID 1258057Notes

Reaction equation

HRID 1258057 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH:6][CH:7]=1)=O.[CH3:13][NH:14][CH3:15].C([BH3-])#N.[Na+].O>CO>[CH3:13][N:14]([CH2:1][C:3]1[CH:4]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH:6][CH:7]=1)[CH3:15]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 321486Ethyl 4-formyl-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 66636781Ethyl 4-[(dimethylamino)methyl]-1H-pyrrole-2-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of ethyl 4-formylpyrrole-2-carboxylate (8.8 g, 52.7 mmol) and dimethylamine (2 M in THF, 40 mL, 1.5 equiv) in methanol (60 mL) was added sodium cyanoborohydride (3.3 g, 1 equiv) in portions and the mixture was stirred for 3 h at 20° C. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with water and dried over Na2SO4. Evaporation of solvent afforded a crude, which was purified by column chromatography on silica gel, eluted with MeOH-DCM (1:9) to afford ethyl 4-dimethylaminomethyl-pyrrole-2-carboxylate as a solid (7.8 g, 76%). MS (ES): 392 (MH+) 197.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customEvaporation of solvent
  5. customafforded a crude, which
  6. customwas purified by column chromatography on silica gel
  7. washeluted with MeOH-DCM (1:9)

Sources & evidence

ORD record
ord-e7db7f45a01c473eb6f3d2006a3e83ad
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

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