Benzyl Bromide → Ethyl 1-benzyl-3-(dibenzylcarbamoyl)-5-oxopyrrolidine-3-carboxylate

HRID 1489159노트

반응식

HRID 1489159 반응식
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][C:10]([C:19](=[O:28])[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][C:10]([C:19](=[O:28])[N:20]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22903655HCID 22903655, 화합물

생성물 1

HCID 22903679Ethyl 1-benzyl-3-(dibenzylcarbamoyl)-5-oxopyrrolidine-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of ethyl 1-benzyl-3-(benzylcarbamoyl)-5-oxopyrrolidine-3-carboxylate obtained in Preparative Example 1 (2) (20 g) in dimethylformamide (20 mI) was added to a mixture of 60% sodium hydride (2.5 g) and dimethylformamide (60 ml) under ice-cooling After the mixture was stirred at room temperature for 1.5 hours, benzyl bromide (9.7 g) was added under ice-cooling and the mixture was starred for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried, concentrated and purified by silica gel column chromatography to give 16.3 g of the object compound as white crystals, melting point 112°-115° C.

후처리

  1. temperaturecooling After the mixture
  2. temperaturecooling
  3. waitthe mixture was starred for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-c87650151bef446580cafa01bbe40bc6
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677316

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