m-Chloroperbenzoic acid → Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 1398024Notes

Reaction equation

HRID 1398024 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=C(C=CC=1)C(OO)=[O:21]>C(Cl)Cl>[CH:3]12[O:21][CH: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 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (5 g, 24.60 mmol) in DCM (80 mL) was added 3-chlorobenzoperoxoic acid (6.89 g, 30.75 mmol) at 0° C. The mixture was then stirred at rt overnight. The reaction mixture was then filtered through a bed of Celite and the filtrate was washed with sat'd aqueous Na2CO3 and brine. The organic was then separated and dried over anhydrous Na2SO4, filtered, and conc. in vacuo to yield the title compound that was used for next step without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered through a bed of Celite
  2. washthe filtrate was washed with sat'd aqueous Na2CO3 and brine
  3. customThe organic was then separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d7202e7f2796400293b4c7b0cdb5141a
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

Loading…