Formamide → 1-Benzylpyrrolidine-3-carboxamide

HRID 854310

反応式

HRID 854310 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 177501551-Benzylpyrrolidine-3-carboxamide

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3776Isopropanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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):

後処理

  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

出典と根拠

ORDレコード
ord-aa762d79698247f081448488da9dcb37
出典データセット
uspto-grants-2007_08
特許番号
US07259157B2

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