Réaction #587447

Équation de réaction

(1-quinolin-6-ylcyclopropyl)acetaldehyde

D-proline

chloroform

N-chlorosuccinimide

→

desired product

1-[2-chloro-1-hydroxy-2-(1-quinolin-6-ylcyclopropyl)ethyl]pyrrolidine-2,5-dione

Conditions de réaction

Traitement

1. 1
   TempératureTo a cooled
2. 2
   Températuregradually warmed to RT for 2 h
3. 3
   AutreThe reaction mixture was quenched with saturated sodium bicarbonate (25 mL)
4. 4
   Extractionextracted with EtOAc (3×100 mL)
5. 5
   LavageThe combined organic layers were washed with brine
6. 6
   Séchagedried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   AutreThe precipitate formed
10. 10
    Filtrationwas filtered

Mode opératoire

To a cooled (0° C.) mixture of (1-quinolin-6-ylcyclopropyl)acetaldehyde (9.9 g, 47 mmol), D-proline (1.1 g, 9.4 mmol) in chloroform (200 mL) was added N-chlorosuccinimide (6.26 g, 46.9 mmol). The mixture was stirred at 0° C. for 30 min and then gradually warmed to RT for 2 h. The reaction mixture was quenched with saturated sodium bicarbonate (25 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The precipitate formed was filtered to give the desired product. The filtrate was chromatographed on silica gel with EtOAc in methylene chloride (10%) to afford chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde which was contaminated with pyrrolidine-2,5-dione (13.0 g), and automatically converted to the desired product after a few days. The total desired product obtained is 16 g. LCMS: (M+H)=345.0/347.0.

Source