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

HRID 62605

Reaction equation

HRID 62605 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e13f7f00e4374bfd90fc6ea29253b12a
Source dataset
uspto-grants-2016_09
Patent number
US09447025B2

Linked notes

Loading…