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

HRID 729448노트

반응식

HRID 729448 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 219790091,3-Dibenzylpyrrolidine-3-carboxylic acid amide수율 103.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-24b354f32447486eba6b1764f5f0006f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

반응 노트

불러오는 중…