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

HRID 1717538Notes

Reaction equation

HRID 1717538 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 C9H15NO3: 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-97d4de66133d4c909008b46623d65305
Source dataset
uspto-grants-2010_09
Patent number
US07803839B2

Reaction notes

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