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

HRID 241713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241713
[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]

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-705ee086c36a4fc98b7c6833478725a1
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653073B2

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