m-Chloroperbenzoic acid → HCID 86638991, compound

HRID 1690862Notes

Reaction equation

HRID 1690862 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]2[CH:11]([O:21]2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53728628HCID 53728628, compound

Product 1

HCID 86638991HCID 86638991, compoundYield 166.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclohex-3-enylmethyl-carbamic acid tert-butyl ester (1.5 g, 7.10 mmol) in ml of anhydrous dichloromethane was added 3-chloroperoxybenzoic acid (2.45 g, 14.2 mmol) under cooling. The resulting mixture was stirred for 19 hours at room temperature and washed with saturated sodium bicarbonate and 0.5M aqueous solution of sodium thiosulphate. The aqueous phase was extracted three times with dichloromethane and the combined organic phases were washed with brine. The resulting organic phase was dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to yield 1.48 g of crude product. Column chromatography of 3.17 g of crude product (silica, petrol ether/ethyl acetate=3/1) resulted in (7-oxa-bicyclo[4.1.0]hept-3-ylmethyl)-carbamic acid tert-butyl ester (Rf=0.19, 2.68 g, 81% yield) as colorless solid.

Workup

  1. temperatureunder cooling
  2. washwashed with saturated sodium bicarbonate and 0.5M aqueous solution of sodium thiosulphate
  3. extractionThe aqueous phase was extracted three times with dichloromethane
  4. washthe combined organic phases were washed with brine
  5. dry with materialThe resulting organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customto yield 1.48 g of crude product

Sources & evidence

ORD record
ord-1909fe2cbfcf4ed8bcb1a947835d00b3
Source dataset
uspto-grants-2012_04
Patent number
US08153689B2

Reaction notes

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