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

HRID 906909ノート

反応式

HRID 906909 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-dee2862cd0824d6390c8e4dce09eb096
出典データセット
uspto-grants-2011_09
特許番号
US08012998B2

反応ノート

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