Tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate → HCID 68953107, Verbindung

HRID 2384930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384930
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[O:21])=[CH:15][CH:16]=1

Komponenten

4

Edukt 1

HCID 67239763Tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 68953107HCID 68953107, VerbindungAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Stir a solution of 3-(4-bromo-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.79 g, 10.7 mmol) in 4 M HCl in dioxane (21.4 mL) at 0° C. for one hour. Concentrate the reaction mixture, dilute the mixture with CH2Cl2, wash with 5 N NaOH (15 mL), and back extract the aqueous with CH2Cl2. Wash the combined organic layer with brine, dry over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph, eluting with 5-10% in MeOH (2N NH3)/CH2Cl2 to give 2.24 g (82%) of the title compound. LC-MS m/z (79Br) 254.0 [M+H]+.

Aufarbeitung

  1. concentrationConcentrate the reaction mixture
  2. additiondilute the mixture with CH2Cl2
  3. washwash with 5 N NaOH (15 mL)
  4. extractionback extract the aqueous with CH2Cl2
  5. washWash the combined organic layer with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude material by flash chromatograph
  10. washeluting with 5-10% in MeOH (2N NH3)/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-296658d0ff634a36a141ca9faa3afee6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263772B2

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