Water → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 358881

Reaction equation

HRID 358881 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH:22]=[CH:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].O>C(Cl)(Cl)Cl>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH:22]2[O:9][CH:21]2[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylateYield 58.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.96 g (0.012 mole) of 70% aqueous m-chloroperbenzoic acid were added to a solution of 1.69 g (0.01 mole) of 1-t-butoxycarbonyl-3-pyrroline [prepared as described in Step (a) above] in 10 ml of chloroform, whilst ice-cooling, and the mixture was stirred with ice-cooling for 8 hours and then with water-cooling for 15 hours. At the end of this time, the reaction mixture was extracted with toluene and the extract was washed, in turn, with an aqueous solution of sodium bicarbonate, a 0.1N aqueous solution of sodium thiosulfate and water. It was then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography eluted with a 1:5 by volume mixture of ethyl acetate and toluene, to afford 1.09 g of 1-t-butoxycarbonyl-3,4-epoxypyrrolidine as a colorless oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling for 8 hours
  3. extractionAt the end of this time, the reaction mixture was extracted with toluene
  4. washthe extract was washed, in turn, with an aqueous solution of sodium bicarbonate
  5. dry with materialIt was then dried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under reduced pressure
  7. washeluted with a 1:5 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-3b5843a477ee452f954ed9e0b498034d
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Linked notes

Loading…