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

HRID 1093978Notes

Reaction equation

HRID 1093978 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-26be5fbff0ba4875b891cd1b4131f5ff
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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