Chloroform → Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 1095677Notes

Reaction equation

HRID 1095677 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)Cl>ClCCl>[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

5

Reactant 3

HCID 6212ChloroformHCID 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

Conditions

Temperature
46 °C

Procedure

Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (11.0 g, 54.1 mmol, commercially available from Aldrich) and 3-chlorobenzoperoxoic acid (17.3 g, 70.4 mmol) were added to 150 mL of chloroform and heated to 46° C. for 20 hours. The mixture was cooled, dichloromethane was added, and the reaction was washed with a saturated solution of NaHCO3 and Na2S2CO3. The combined organic layers were dried over MgSO4, filtered and concentrated to give 10.5 g (88% isolated yield) of the desired compound as an oil, which was used directly in the next step.

Workup

  1. temperatureThe mixture was cooled
  2. washthe reaction was washed with a saturated solution of NaHCO3 and Na2S2CO3
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give

Sources & evidence

ORD record
ord-fa428ffab71f4dcc84dc2f0e5e18f81d
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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