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

HRID 1257918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257918
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([CH2:14][CH:15]=[O:16])[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1CCC[C@@H]1C(O)=O.Cl[N:26]1[C:30](=[O:31])[CH2:29][CH2:28][C:27]1=[O:32].C(Cl)(Cl)[Cl:34]>>[Cl:34][CH:14]([C:11]1([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)[CH2:12][CH2:13]1)[CH:15]([N:26]1[C:30](=[O:31])[CH2:29][CH2:28][C:27]1=[O:32])[OH:16]

Komponenten

5

Edukt 4

HCID 6212ChloroformHCID 8988D-ProlineHCID 31398ChlorosuccinimideHCID 86621505(1-Quinolin-6-ylcyclopropyl)acetaldehyde

Produkt 1

HCID 672238331-[2-Chloro-1-hydroxy-2-(1-quinolin-6-ylcyclopropyl)ethyl]pyrrolidine-2,5-dione

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureTo a cooled
  2. temperaturegradually warmed to RT for 2 h
  3. customThe reaction mixture was quenched with saturated sodium bicarbonate (25 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe precipitate formed
  10. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-98422e5cbc414002bf435dfff8081167
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461330B2

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