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

HRID 44258Notes

Reaction equation

HRID 44258 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].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[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

4

Reactant 3

HCID 674DimethylamineHCID 321486Ethyl 4-formyl-1H-pyrrole-2-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66636781Ethyl 4-[(dimethylamino)methyl]-1H-pyrrole-2-carboxylate

Procedure

To a solution of the compound obtained in Step C and dimethylamine (1.1 eq.) there is added, in portions, NaBH(OAc)3 (952 mg). The mixture is stirred overnight at ambient temperature. After evaporation to dryness, the residue is taken up in CH2Cl2 and water. The aqueous phase is extracted with CH2Cl2. The organic phases are combined and then extracted with aqueous 1N HCl solution. The aqueous phase is made alkaline and is then extracted with CH2Cl2. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness to yield the title product, which is used directly in the next Step.

Workup

  1. customAfter evaporation to dryness
  2. extractionThe aqueous phase is extracted with CH2Cl2
  3. extractionextracted with aqueous 1N HCl solution
  4. extractionis then extracted with CH2Cl2
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-38deb3fecf3a44d6b9b58eb218668e48
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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