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HRID559290

反应详情

EQUATION

反应方程式

HRID 559290 反应方程式

REACTANTS

反应物

3
Sodium hydride 分子结构式
HCID24758

Sodium hydride

HNa

2-Chloro-5-cyanopyridine 分子结构式
HCID5152094

2-Chloro-5-cyanopyridine

C6H3ClN2

HCID 66999687 分子结构式
HCID66999687

未命名化合物

PRODUCTS

产物

1
6-{(SR)-1-[(3RS,4SR)-1-Benzyl-4-(4-cyano-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile 分子结构式
HCID66999603

6-{(SR)-1-[(3RS,4SR)-1-Benzyl-4-(4-cyano-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

C26H24N4O

收率 45%

AUXILIARIES

试剂、催化剂与溶剂

1
Dimethylformamide 分子结构式
溶剂HCID6228

Dimethylformamide

C3H7NO

PROCEDURE

实验过程

To a stirred solution of 4-[(3SR,4RS)-1-benzyl-4-((SR)-1-hydroxy-ethyl)-pyrrolidin-3-yl]-benzonitrile (V-A-5) (0.65 g, 2.12 mmol) in DMF (40 mL) at RT was added NaH (55% purity, 0.10 g, 4.1 mmol). After 10 minutes, 6-chloro-nicotinonitrile (0.32 g, 2.33 mmol) was added. The reaction mixture was stirred over night at RT, filtered on celite and concentrated under vacuo. Extraction with EtOAc/aq.NH4Cl sat, followed by column chromatography (SiO2, EtOAc/H, 1:1) yielded 0.39 g (45%) of the title compound as a colorless oil. ES-MS m/e: 409.3 (M+H+).

WORKUP

后处理

  1. filtrationfiltered on celite
  2. concentrationconcentrated under vacuo
  3. extractionExtraction with EtOAc/aq