m-Chloroperbenzoic acid → 1,1-Dimethylethyl 3-(2-oxiranyl)-1-pyrrolidinecarboxylate

HRID 358903Notes

Reaction equation

HRID 358903 reaction equation
ClC1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)C=1.[C:12]([O:16][C:17]([N:19]1CCC(=C)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(Cl)(Cl)Cl>[C:12]([O:16][C:17]([N:19]1[CH2:7][CH2:6][CH:5]([CH:4]2[O:10][CH2:8]2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 15297967tert-Butyl 3-methylidenepyrrolidine-1-carboxylate

Product 1

HCID 200671521,1-Dimethylethyl 3-(2-oxiranyl)-1-pyrrolidinecarboxylateYield 56.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.54 g (0.0175 mole) of 85% m-chloroperbenzoic acid were added to a solution of 2.67 g (0.0146 mole) of 1-t-butoxycarbonyl-3-methylenepyrrolidine [prepared as described in Step (4) above] in 20 ml of chloroform, whilst ice-cooling, and the mixture was stirred at the same temperature for 6 hours and then stirred at room temperature overnight. At the end of this time, 1.8 g (0.073 mole) of 70% m-chloroperbenzoic acid were added, and the mixture was stirred at room temperature for 12 hours. At the end of this time, the mixture was extracted with toluene. The toluene extract was washed, in turn, with an aqueous solution of sodium bicarbonate, with an aqueous solution of sodium thiosulfate and with water, in that order, after which it was dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel eluted with a 1:9 by volume mixture of ethyl acetate and toluene, to give 1.77 g of 1-t-butoxycarbonyl-3 -(1,2-epoxyethyl)pyrrolidine as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature overnight
  3. stirringthe mixture was stirred at room temperature for 12 hours
  4. extractionAt the end of this time, the mixture was extracted with toluene
  5. extractionThe toluene extract
  6. washwas washed, in turn, with an aqueous solution of sodium bicarbonate, with an aqueous solution of sodium thiosulfate and with water, in that order
  7. customafter which it was dried
  8. concentrationconcentrated by evaporation under reduced pressure
  9. washeluted with a 1:9 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-bb0df611152847e4ac0fe7489f277331
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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