1,2-Dichloroethane → 1-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-1-(6-methoxy-pyridine-3-carbonyl)-pyrrolidin-3-yl]-ethanone

HRID 906909노트

반응식

HRID 906909 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]2[CH2:45][NH:44][CH2:43][CH:42]2[C:46](=[O:48])[CH3:47])[CH:37]=[CH:38][C:39]=1[Cl:40]>C(Cl)Cl>[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]2[CH2:45][N:44]([C:7]([C:6]3[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[O:9])[CH2:43][CH:42]2[C:46](=[O:48])[CH3:47])[CH:37]=[CH:38][C:39]=1[Cl:40]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5924996-Methoxynicotinic acidHCID 671317481-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethanone

생성물 1

HCID 671314081-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-1-(6-methoxy-pyridine-3-carbonyl)-pyrrolidin-3-yl]-ethanone수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 6-methoxy-nicotinic acid (0.53 g, 3.40 mmol) in CH2Cl2 (15 mL) were added EDC (0.659 g, 3.40 mmol), HOBt (0.465 g, 3.40 mmol) and Et3N (0.59 mL, 4.3 mmol). After one hour at RT was added 1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanone (XIII-1) (0.74 g, 2.90 mmol) and stirring was continued over night. The reaction mixture was then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrate under vacuo. Flash chromatography (SiO2, EtOAc/H, 1:1) afforded 0.64 g (57%) of the title product as a white solid. ES-MS m/e: 393.1 (M+H+).

후처리

  1. waitwas continued over night
  2. additionThe reaction mixture was then poured onto water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrate under vacuo

출처 및 근거

ORD 기록
ord-dee2862cd0824d6390c8e4dce09eb096
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012998B2

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