HRID1453010

反应详情

EQUATION

反应方程式

HRID 1453010 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

2-Chloro-4-6-dimethoxy-1,3,5-triazine (2.68 g, 15.2 mmol) and N-methylmorpholine (4.2 mL, 38.1 mmol) were added to a solution of 3-(2-Oxo-pyrrolidin-1-yl)-propionic acid (2 g, 12.7 mmol, from Step 1) in THF (35 mL). After 1 h the reaction mixture was filtered through a glass frit to remove a white precipitate. The filtrate was treated with copper iodide (2.4 g, 12.7 mmol), cooled to 0° C. and then cyclopentyl magnesium bromide (6.35 mL, 12.7 mmol, 2M in ether) was added. After 4 h the resulting black mixture was quenched with saturated NH4Cl and extracted with CH2Cl2. The organic layers were washed with 1N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purifed by silica gel chromatography (75% EtOAc in hexanes then 5% MeOH in CH2Cl2) to give the title compound as a yellow oil. (0.4 g, 15% yield). 1H NMR (CDCl3): δ 1.55-1.83 (br m, 8H), 1.99 (m, 3H), 2.35 (t, 2H, J=8.3 Hz), 2.74 (t, 2H, J=6.8 Hz), 3.41 (d, 2H, J=7.2 Hz), 3.53 (t, 2H, J=6.6 Hz).

WORKUP

后处理

  1. filtrationAfter 1 h the reaction mixture was filtered through a glass frit
  2. customto remove a white precipitate
  3. customAfter 4 h the resulting black mixture was quenched with saturated NH4Cl
  4. extractionextracted with CH2Cl2
  5. washThe organic layers were washed with 1N HCl, saturated NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated