Diisopropylethylamine → 3-Cyclohexyl-1-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one

HRID 1670836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670836
Br[CH2:2][CH2:3][CH:4]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:5]([NH:7][CH2:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([O:16][CH3:17])=[CH:11][C:10]=1[Cl:18])=[O:6].C(N(C(C)C)CC)(C)C>C1COCC1.C(OC(=O)C)C>[CH:19]1([CH:4]2[CH2:3][CH2:2][N:7]([CH2:8][C:9]3[C:14]([Cl:15])=[CH:13][C:12]([O:16][CH3:17])=[CH:11][C:10]=3[Cl:18])[C:5]2=[O:6])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

5

Edukt 2

HCID 81531DiisopropylethylamineHCID 673563304-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

Produkt 1

HCID 576580123-Cyclohexyl-1-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-oneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Treat a solution of 4-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide (2.0 g, 4.6 mmol) in THF (30 mL) with diisopropyl ethyl amine (1.19 g, 9.19 mmol) at 40° C. for 12 hours and at reflux for 6 hours. Cool the reaction, dilute with ethylacetate and wash with HCl (1N) and water. After drying the organic layer over sodium sulfate, filtrate and concentrate under vacuum. Purify the residue by silica gel chromatography with 1:4 ethyl acetate:hexane to afford 1.3 g (80%) of the title compound. MS (m/z): 356 (M+).

Aufarbeitung

  1. temperatureat reflux for 6 hours
  2. temperatureCool
  3. customthe reaction
  4. washwash with HCl (1N) and water
  5. dry with materialAfter drying the organic layer over sodium sulfate, filtrate
  6. concentrationconcentrate under vacuum
  7. customPurify the residue by silica gel chromatography with 1:4 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4a72a2cacc964d179273eefcb7f3d378
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994176B2

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