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

HRID 582528Notes

Reaction equation

HRID 582528 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]([O:16][C:17]([N:19]1[CH2:23][CH:22]=[CH:21][CH2:20]1)=[O:18])([CH3:15])[CH3:14].C(OCC)(=O)C>ClCCl>[CH3:15][C:13]([CH3:12])([O:16][C:17]([N:19]1[CH2:23][CH:22]2[CH:21]([O:9]2)[CH2:20]1)=[O:18])[CH3:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 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 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

80% m-Chloroperbenzoic acid (3.9 g, 0.0226 mole) was added to a solution of 2,5-dihydro-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester (3.55 g, 0.021 mole) in dichloromethane (70 ml) and the mixture was stirred for 24h when more peracid (0.27 g,0.00156 mole) was added and the stirring continued for a further 4h. Ethyl acetate was added and the mixture was washed with 10% sodium carbonate solution. The aqueous phase was extracted with ethyl acetate (50 ml) and the combined organic solution washed with water, dried (MgSO4) and evaporated to leave an oil which was purified by column chromatography on flash silica eluting with 30% ethyl acetate in cyclohexane to give the title compound (1.52 g) as an oil, nmr(δ,CDCl3) includes 1.45(s,9H), 3.42(dd,2H), 3.67(s,2H), 3.78(dd,2H).

Workup

  1. additionwas added
  2. washthe mixture was washed with 10% sodium carbonate solution
  3. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
  4. washthe combined organic solution washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto leave an oil which
  8. customwas purified by column chromatography on flash silica eluting with 30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-b4b04a008001403f9d7eb62bbb8c6517
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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