Methanol → 8-((3aS,6aS)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-3-(phenylsulfonyl)-quinoline

HRID 2092194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092194
[C:1]1([S:7]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]2[CH2:24][CH2:23][C@H:22]3[CH2:25][N:26](C(OCC)=O)[CH2:27][C@@H:21]23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](I)(C)C.CO>C(Cl)(Cl)Cl>[N:20]1([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[CH:11][C:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])=[CH:19]3)[CH2:24][CH2:23][C@H:22]2[CH2:25][NH:26][CH2:27][C@@H:21]12

Komponenten

5

Edukt 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 25196275(3aS,6aS)-ethyl 1-(3-(phenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Produkt 1

HCID 251963888-((3aS,6aS)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-3-(phenylsulfonyl)-quinolineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of (3aS,6aS)-ethyl 1-(3-(phenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (60 mg, 0.133 mmol) and trimethylsilyl-iodide (160 mg, 0.797 mmol) in chloroform (1 mL) was stirred at reflux for 1.5 h. Methanol (4 mg) was added and the solution was partitioned between ethyl acetate and aqueous NaOH (1M). The organic extract was dried (MgSO4), filtered and concentrated to yield 11 mg (22%) of the title compound as a pale yellow oil.

Aufarbeitung

  1. temperatureat reflux for 1.5 h
  2. customthe solution was partitioned between ethyl acetate and aqueous NaOH (1M)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2d1669404e6949be95e2b2f745333d88
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440694B2

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