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

HRID 500265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500265
[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-9aa937dddc4e4064a602720070d4e865
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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