Acetyl chloride → 3-Acetamidobicyclo[1.1.1]pentan-1-yl acetate

HRID 62605

Reaktionsgleichung

Reaktionsgleichung von HRID 62605
[C:1]([O:4][C:5]12[CH2:9][C:7]([NH2:10])([CH2:8]1)[CH2:6]2)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].[C:16](Cl)(=[O:18])[CH3:17]>CN(C=O)C>[C:1]([O:4][C:5]12[CH2:9][C:7]([NH:10][C:16](=[O:18])[CH3:17])([CH2:8]1)[CH2:6]2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 904111873-Aminobicyclo[1.1.1]pentan-1-yl acetate

Produkt 1

HCID 862879553-Acetamidobicyclo[1.1.1]pentan-1-yl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a DMF (2 mL) solution of 3-aminobicyclo[1.1.1]pentan-1-yl acetate (1 mmol) is added sodium bicarbonate (3 mmol) and then acetyl chloride (1 mmol) by syringe at 0° C. The reaction is allowed to warm up to room temperature and monitored by LCMS. After LCMS analysis indicated consumption of starting material, the reaction is diluted with water and extracted with EtOAc (3×). The organic layers are combined, washed with brine, dried (magnesium sulfate), filtered, and concentrated. The crude residue is subjected to flash chromatography (silica gel, EtOAc/hexanes) to give 3-acetamidobicyclo[1.1.1]pentan-1-yl acetate (3).

Aufarbeitung

  1. customat 0° C
  2. customconsumption of starting material
  3. additionthe reaction is diluted with water
  4. extractionextracted with EtOAc (3×)
  5. washwashed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e13f7f00e4374bfd90fc6ea29253b12a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447025B2

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