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

HRID 1694867Notes

Reaction equation

HRID 1694867 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-ba69888c4b4d4f279910ff83a2fdbc32
Source dataset
uspto-grants-2012_04
Patent number
US08158797B2

Reaction notes

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