Ethyl Acetate → 1-[(5-Bromo-2-thienyl)sulfonyl]pyrrolidine

HRID 656144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656144
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>ClCCl.[Cl-].[Na+].O>[Br:1][C:2]1[S:6][C:5]([S:7]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Produkt 1

HCID 8939391-[(5-Bromo-2-thienyl)sulfonyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

5-Bromo-2-thiophenesulfonyl chloride (523 mg, 2 mmol) was dissolved in dichloromethane (20 mL). Pyrrolidine (213 mg, 3 mmol) and potassium carbonate (829 mg, 6 mmol,) are added, and the mixture was stirred at 23° C. for 1 h. After tlc (30% ethyl acetate in hexanes) indicated that the reaction had gone to completion, brine was added and the mixture was extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated. The crude product was purified by isco combiflash, eluting with 0-50% ethyl acetate in hexanes (40 g column), giving the title compound.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by isco combiflash
  7. washeluting with 0-50% ethyl acetate in hexanes (40 g column)

Quellen und Nachweise

ORD-Eintrag
ord-345cf1749a9344b184dc0bf0e35b26e5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071584B2

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