Iodoethane → N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

HRID 62619

Reaktionsgleichung

Reaktionsgleichung von HRID 62619
[OH:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2.[H-].[Na+].I[CH2:14][CH3:15]>C1COCC1>[CH2:14]([O:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2)[CH3:15]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86287953N-{3-hydroxybicyclo[1.1.1]pentan-1-yl}acetamide

Produkt 1

HCID 86287954N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a anhydrous THF (5 mL) solution of N-(3-hydroxybicyclo[1.1.1]pentan-1-yl)acetamide (1) (1 mmol) is added NaH (60% dispersion in mineral oil, 3 mmol) portionwise at 0° C. After addition, the mixture is stirred until the evolution of gas stops. Iodoethane (1 mmol) is then added by syringe slowly. The reaction is monitored by LCMS and TLC. After consumption of starting material, the reaction mixture is quenched by adding water (3 mL) and extracted with ethyl acetate (3×). The organic layers are combined, dried (magnesium sulfate), filtered, and concentrated. The crude residue is subjected to flash chromatography (silica gel, EtOAc/hexanes) to afford compound 2.

Aufarbeitung

  1. additionAfter addition
  2. customAfter consumption of starting material
  3. customthe reaction mixture is quenched
  4. additionby adding water (3 mL)
  5. extractionextracted with ethyl acetate (3×)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-45c14c917c764965805b0182053a9dda
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447026B2

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