Formamide → 1-Benzylpyrrolidine-3-carboxamide

HRID 854310

Reaktionsgleichung

Reaktionsgleichung von HRID 854310
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6]1)=O.C([NH2:19])=O.C[O-].[Na+].[Na]>CN(C=O)C.CO.C(O)(C)C>[CH2:10]([N:7]1[CH2:8][CH2:9][CH:5]([C:3]([NH2:19])=[O:2])[CH2:6]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

8

Edukt 4

HCID 713FormamideHCID 4610751Methyl 1-benzylpyrrolidine-3-carboxylateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Produkt 1

HCID 177501551-Benzylpyrrolidine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 4.4 g of 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (M. J. Kornet et al., J. Org. Chem., 33:3637–3639(1968)) and 3 g of formamide in 10 mL of anhydrous DMF heated to 100° C. was added a solution of sodium methoxide, from 0.33 g of sodium dissolved in methanol, dropwise over 20 min. After stirring for 1 h at 100° C., the mixture was allowed to cool to rt and added to 100 mL of isopropanol. The mixture was concentrated to dryness. The resulting residue was triturated with 200 mL of chloroform, filtered and concentrated to dryness under reduced pressure. The resulting oil was fairly homogeneous by TLC (development with 90:10 chloroform saturated with ammonia: methanol):

Aufarbeitung

  1. temperatureto cool to rt
  2. concentrationThe mixture was concentrated to dryness
  3. customThe resulting residue was triturated with 200 mL of chloroform
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aa762d79698247f081448488da9dcb37
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259157B2

Verknüpfte Notizen

Wird geladen…