huagongshe.com
HRID1670619

反应详情

EQUATION

反应方程式

HRID 1670619 的结构方程式

REACTANTS

反应物

3
结构：CCN(CC)CC
HCID8471

Triethylamine

C6H15N

结构：O=[N+]([O-])c1cc(Br)ccc1F
HCID2736328

4-Bromo-1-fluoro-2-nitrobenzene

C6H3BrFNO2

结构：CC(C)(C)OC(=O)N1C[C@H](NCc2ccccc2)[C@@H](O)C1
HCID11277777

tert-Butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

C16H24N2O3

PRODUCTS

生成物

1
结构：CC(C)(C)OC(=O)N1C[C@H](Nc2ccc(Br)cc2[N+](=O)[O-])[C@@H](O)C1
HCID67333783

未命名化合物

收率 94.6%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CCOC(C)=O
溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To a solution of 1-bromo-4-fluoro-3-nitrobenzene (0.125 mol, 26.0 g) in ethyl acetate (300 mL) add (3S,4S)-3-benzylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.113 mol, 23.0 g) and triethylamine (0.339 mol, 35.0 g), reflux for 14 h, cool to room temperature, and wash with water and brine. Dry over anhydrous sodium sulfate, evaporate the solvent, and purify by flash column chromatography to give the title compound as a yellow solid (43.0 g, 90%). APCI MS m/z 403 [M+H]+.

WORKUP

后处理

  1. temperaturereflux for 14 h
  2. washwash with water and brine
  3. dry with materialDry over anhydrous sodium sulfate
  4. customevaporate the solvent
  5. custompurify by flash column chromatography