m-Chloroperbenzoic acid → HCID 11252963, compound

HRID 712512Notes

Reaction equation

HRID 712512 reaction equation
[N:1]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[C@H:3]12[O:24][C@H:4]1[CH2:5][N:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 643471Benzyl 3-pyrroline-1-carboxylate

Product 1

HCID 11252963HCID 11252963, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (2.00 g, 9.80 mmol) in CH2Cl2 (10 mL) was added slowly 3-chloroperbenzoic acid (3.00 g, 14.80 mmol) at 0° C. The reaction mixture was stirred for 13 h at room temperature, then quenched with saturated sodium thiosulfate aqueous solution and extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 6:1 (v/v) PE/EtOAc) to give the title compound as colorless oil (1.75 g, 81.02%).

Workup

  1. customquenched with saturated sodium thiosulfate aqueous solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed with a silica gel column (eluting agent: 6:1 (v/v) PE/EtOAc)

Sources & evidence

ORD record
ord-57cd8f593b0943b89ab1b58a86f7d3d4
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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