m-Chloroperbenzoic acid → Benzyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

HRID 2387582Notes

Reaction equation

HRID 2387582 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13](=[CH2:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:18].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl.S([O-])([O-])=O.[Na+].[Na+]>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]2([O:18][CH2:16]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 184122471-Cbz-3-methylenepyrrolidine

Product 1

HCID 71649494Benzyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24437Sodium SulfiteSolvent

Procedure

A solution 3-methylen-pyrrolidine-1-carboxylic acid benzyl ester (WO9624593) in 5 ml of dichloromethane was treated with 2.16 g sodium bicarbonate (MW: 84.01 26.28 mmol) and 2.47 g of 80% m-chlor-perbenzoic acid (MW: 172.57, 11.48 mmol). The reaction mixture was stirred at room temperature for three hours. The reaction mixture was diluted with 20 ml of a saturated, aqueous sodium sulfite solution and 45 ml of dichloromethane. The organic layer was successively washed with 30 ml of an aqueous saturated sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate. The residue was purified by chromatography on silica (1/1 ethyl acetate/n-hexane) to afford a off white solid. Yield: 440 mg, 57%. MS: 234.1 (M+H)+, Method ESI+.

Workup

  1. washThe organic layer was successively washed with 30 ml of an aqueous saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe residue was purified by chromatography on silica (1/1 ethyl acetate/n-hexane)
  4. customto afford a off white solid

Sources & evidence

ORD record
ord-6bdd3300cb0441e99a3633965d343f16
Source dataset
uspto-grants-2012_09
Patent number
US08268812B2

Reaction notes

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