m-Chloroperbenzoic acid → 3-Aminobicyclo[1.1.1]pentan-1-yl acetate

HRID 62616Notes

Reaction equation

HRID 62616 reaction equation
[NH2:1][C:2]12[CH2:6][C:4](C(=O)C)([CH2:5]1)[CH2:3]2.ClC1C=CC=[C:13]([C:17]([O:19]O)=[O:18])C=1>C(Cl)(Cl)Cl>[C:17]([O:19][C:4]12[CH2:3][C:2]([NH2:1])([CH2:5]1)[CH2:6]2)(=[O:18])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 904108111-{3-Aminobicyclo[1.1.1]pentan-1-yl}ethan-1-one

Product 1

HCID 904111873-Aminobicyclo[1.1.1]pentan-1-yl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-(3-aminobicyclo[1.1.1]pentan-1-yl)ethanone (1 mmol) in 0.5 mL of chloroform is added to a stirred mixture of m-chloroperbenzoic acid (1.5 mmol) in 2 mL of chloroform at r.t. The solution is stirred in the dark for 24 h. The mixture is filtered, and the filtrate is washed with 10% sodium bicarbonate and then water. The organic layer is dried over magnesium sulfate and concentrated. The residue is purified by a flash chromatography on silica gel (EtOAc/hexanes) to give 3-aminobicyclo[1.1.1]pentan-1-yl acetate.

Workup

  1. filtrationThe mixture is filtered
  2. washthe filtrate is washed with 10% sodium bicarbonate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by a flash chromatography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-fbe27a3421344dafa5cf76d7e07b9798
Source dataset
uspto-grants-2016_09
Patent number
US09447026B2

Reaction notes

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