N-Methylmaleimide → 4-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-2-methyloctahydropyrrolo[3,4-a]-indolizine-1,3-dione

HRID 540638

Reaktionsgleichung

Reaktionsgleichung von HRID 540638
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[CH:16]=O)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:18]1[CH2:23][C@H:22]([C:24](O)=O)[NH:21][CH2:20][CH2:19]1.[CH3:27][N:28]1[C:32](=[O:33])C=[CH:30][C:29]1=[O:34]>CC#N>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[CH:16]3[N:21]4[CH:22]([CH2:23][CH2:18][CH2:19][CH2:20]4)[CH:24]4[C:32](=[O:33])[N:28]([CH3:27])[C:29](=[O:34])[CH:30]34)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 70261N-MethylmaleimideHCID 736316Pipecolic acid, (+)-HCID 86676729(E)-3-[5-(3-Fluorophenyl)pyridin-2-yl]propenal

Produkt 1

HCID 534923674-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-2-methyloctahydropyrrolo[3,4-a]-indolizine-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 235 mg of (E)-3-[5-(3-fluorophenyl)pyridin-2-yl]propenal, 133 mg of D-pipecolinic acid, 115 mg of N-methylmaleimide and 30 ml of MeCN is heated at the boil for 2 h. The volatile components are removed under reduced pressure and the residue is purified by column chromatography (silica gel, MeOH:DCM=97:3). In this manner, 2 pure fractions are isolated.

Aufarbeitung

  1. temperatureis heated at the boil for 2 h
  2. customThe volatile components are removed under reduced pressure
  3. customthe residue is purified by column chromatography (silica gel, MeOH:DCM=97:3)
  4. customIn this manner, 2 pure fractions are isolated

Quellen und Nachweise

ORD-Eintrag
ord-3857c9eaa0c34ea8a260062be61b4bfb
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871798B2

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