m-Chloroperbenzoic acid → Tert-butyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylate

HRID 1808942Notes

Reaction equation

HRID 1808942 reaction equation
[CH2:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)(Cl)Cl>[O:18]1[C:2]2([CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]2)[CH2:1]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 55269097tert-Butyl 3-methylideneazetidine-1-carboxylate

Product 1

HCID 66521770Tert-butyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-methylideneazetidine-1-carboxylate (2.96 g, 17.5 mmol) in chloroform (180 mL) was added 3-chloroperoxybenzoic acid (77%, 13.9 g, 62.0 mmol), and the resulting mixture was stirred at room temperature for 2 days. The reaction mixture was quenched with a 1:1 mixture (150 mL) of 10% sodium thiosulfate and saturated sodium bicarbonate solutions. The organic portion was isolated, dried over sodium sulfate, filtered and concentrated to give an oily residue which was then purified by flash chromatography (15-50% ethyl acetate-hexanes) to give 1,1-dimethylethyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylate (1.65 g, 51%), GC-MS for C9H5NO3: 185.

Workup

  1. customThe reaction mixture was quenched with a 1:1 mixture (150 mL) of 10% sodium thiosulfate and saturated sodium bicarbonate solutions
  2. customThe organic portion was isolated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oily residue which
  7. customwas then purified by flash chromatography (15-50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-643b9f238c514c28bdee2b9f67f0e72f
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

Loading…