m-Chloroperbenzoic acid → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 1162631Notes

Reaction equation

HRID 1162631 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:12][CH:11]2[CH:10]([O:21]2)[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10844857tert-Butyl 2,3-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

22.1 A solution of 19.6 g N-Boc-pyrroline in 200 ml CH2Cl2 was cooled to −10° C. and was treated in two portions with 30 g meta-chloroperbenzoic acid. The mixture was stirred for 17 h, slowly warming up to room temperature. Then, the white precipitate was filtered off and washed with dichloromethane. The filtrate was washed with 5% aq. NaHSO3, sat. aq. NaHCO3 and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 65:35) to give 11.8 g 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester as a light yellow oil. MS 186.1 ([M+H]+)

Workup

  1. filtrationThen, the white precipitate was filtered off
  2. washwashed with dichloromethane
  3. washThe filtrate was washed with 5% aq. NaHSO3, sat. aq. NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 65:35)

Sources & evidence

ORD record
ord-ef9bd99c2d1d42caa15bd5fc70710537
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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