N-Cyclohexyl-2-pyrrolidone → HCID 11645326, Verbindung

HRID 1173829

Reaktionsgleichung

Reaktionsgleichung von HRID 1173829
[CH:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:22][C:23]1[S:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[CH:24]=1>C1COCC1>[S:27]1[C:23]([CH2:22][CH:9]2[CH2:10][CH2:11][N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:8]2=[O:12])=[CH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]1=2

Komponenten

5

Edukt 3

HCID 81278N-Cyclohexyl-2-pyrrolidoneHCID 2724682Lithium diisopropylamideHCID 136426052-(Bromomethyl)benzo[b]thiophene

Produkt 1

HCID 11645326HCID 11645326, VerbindungAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Place 1-cyclohexyl-pyrrolidin-2-one (500 mg) in THF (30 mL) and cool to −78° C. Slowly add lithium diisopropylamide (LDA) (2M, 1.5 eq) and stir for 15 minutes. Add 2-bromomethyl-benzo[b]thiophene [J. Med. Chem. (1992) 1176-1183] (815 mg, 3.59 mmol) and stir for 3 hours. Quench with ammonium chloride and extract with dichloromethane. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-50% ethyl acetate in hexanes) to give 670 mg, 71% of the title compound as a white powder. MS (APCI-pos mode) m/z (rel intensity) 314 (100).

Aufarbeitung

  1. customQuench with ammonium chloride
  2. extractionextract with dichloromethane
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel (20-50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b64bfa3151314357a4245bf87be67758
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834194B2

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