Triethylamine → 1,3-Dibenzylpyrrolidine-3-carboxylic acid amide

HRID 729448ノート

反応式

HRID 729448 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:13](O)=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:25]1C=CN=C1)=O.C(N(CC)CC)C.[NH4+].[OH-]>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:13]([NH2:25])=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 219793511,3-Dibenzylpyrrolidine-3-carboxylic acid

生成物 1

HCID 219790091,3-Dibenzylpyrrolidine-3-carboxylic acid amide収率 103.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 1,3-dibenzylpyrrolidine-3-carboxylic acid (Example A28, 4.0 g, 13.5 mmol), 1,1′-carbonyldiimidazole (2.42 g, 14.9 mmol), and triethylamine (2.08 mL, 14.9 mmol) in tetrahydrofuran (100 mL) is heated at reflux for 1.5 hours. The solution is cooled, poured into NH4OH (300 mL), and stirred for 18 hours. The mixture is extracted with chloroform, the organic layer is washed with water, dried, and concentrated to afford 4.13 g of the title compound as an oil; MS EI+: m/z 295 (MH+).

後処理

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe solution is cooled
  4. extractionThe mixture is extracted with chloroform
  5. washthe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-24b354f32447486eba6b1764f5f0006f
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

反応ノート

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