m-Chloroperbenzoic acid → HCID 86638991, compound

HRID 656220Notes

Reaction equation

HRID 656220 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 20 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-19622efb7971439a904b8d58aa85f2f3
Source dataset
uspto-grants-2011_12
Patent number
US08071643B2

Reaction notes

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