m-Chloroperbenzoic acid → 1-Oxa-5-azaspiro[2.3]hexane-5-carboxylic acid phenylmethyl ester

HRID 1672867Notes

Reaction equation

HRID 1672867 reaction equation
[CH2:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:3]1.ClC1C=C(C=CC=1)C(OO)=[O:21]>C(Cl)(Cl)Cl>[O:21]1[C:2]2([CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])[CH2:3]2)[CH2:1]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67051849Benzyl 3-methyleneazetidine-1-carboxylate

Product 1

HCID 594692221-Oxa-5-azaspiro[2.3]hexane-5-carboxylic acid phenylmethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of phenylmethyl 3-methylideneazetidine-1-carboxylate (2.46 g, 0.0121 mol) in chloroform (100 mL) was added 3-chloroperoxybenzoic acid (12.5 g, 0.0726 mol) at 0° C. The reaction mixture was allowed to warm up to room temperature over a period of 12 hours then quenched with 1 M sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1). The layers were separated and the organic layer was dried over anhydrous magnesium sulfate then concentrated. The residue was purified by flash chromatography (5-15% ethyl acetate in hexanes) to afford phenylmethyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylate (2.2 g, 83% yield) as clear and colorless oil. 1H NMR (400 MHz, CDCl3): 7.37-7.29 (m, 5H), 5.12 (s, 2H), 4.35-4.26 (m, 4H), 2.85 (s, 2H). MS (EI) for C12H13NO3: 220 (MH+).

Workup

  1. customthen quenched with 1 M sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationthen concentrated
  5. customThe residue was purified by flash chromatography (5-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3b73a99103b84d3fb4eb940e0901abe0
Source dataset
uspto-grants-2011_08
Patent number
US07999006B2

Reaction notes

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