Formamide → 1-Benzylpyrrolidine-3-carboxamide

HRID 1827184Notes

Reaction equation

HRID 1827184 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 177501551-Benzylpyrrolidine-3-carboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4.4 g 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (M. J. Kornet, P. A. Thio, S. E. Tan, J. Organic Chemistry, 33:3637–3639(1968) and 3 g formamide in 10 mL of anhydrous DMF heated to 100° C., a solution of sodium methoxide, from 0.33 g of sodium dissolved in methanol, was added dropwise over 20 minutes. After stirring for 1 h at 100° C., the mixture was allowed to cool to room temperature and added to 100 mL of isopropanol. The mixture was concentrated to dryness. The 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):

Workup

  1. additionwas added dropwise over 20 minutes
  2. temperatureto cool to room temperature
  3. concentrationThe mixture was concentrated to dryness
  4. customThe residue was triturated with 200 mL of chloroform
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6b2f5fc5ab364b50a672ed5edf986886
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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