Vinyl chloroformate → (3aRS,7SR,7aRS)-7-methyl-7-phenyl-2-vinyloxycarbonyl-4-perhydroisoindolone

HRID 55416

Reaction equation

HRID 55416 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([CH3:24])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)C1C=CC=CC=1.Cl[C:26]([O:28][CH:29]=[CH2:30])=[O:27]>ClCCCl>[CH3:24][C:11]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]2[CH:15]([CH2:16][N:8]([C:26]([O:28][CH:29]=[CH2:30])=[O:27])[CH2:9]2)[C:14](=[O:17])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 67714154(3aRS,7SR,7aRS)-2-benzyl-7-methyl-7-phenyl-4-perhydroisoindolone

Product 1

HCID 67714243(3aRS,7SR,7aRS)-7-methyl-7-phenyl-2-vinyloxycarbonyl-4-perhydroisoindolone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 9 g of (3aRS,7SR,7aRS)-2-benzyl-7-methyl-7-phenyl-4-perhydroisoindolone in 100 cm3 of 1,2-dichloroethane are added, at room temperature, 2.84 cm3 of vinyl chloroformate, followed by heating for 2 hours at reflux. The solution is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is purified by chromatography on a Column of silica gel (particle size 0.04-0.06 mm, diameter 4 cm, height 23 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (90/10 by volume) and collecting 100 cm3 fractions. Fractions 17 to 34 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 4.27 g of (3aRS,7SR,7aRS)-7-methyl-7-phenyl-2-vinyloxycarbonyl-4-perhydroisoindolone are obtained in the form of a yellow oil.

Workup

  1. temperatureby heating for 2 hours
  2. temperatureat reflux
  3. concentrationThe solution is concentrated to dryness under reduced pressure (2.7 kPa)
  4. customthe residue is purified by chromatography on a Column of silica gel (particle size 0.04-0.06 mm, diameter 4 cm, height 23 cm)
  5. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (90/10 by volume)
  6. customcollecting 100 cm3 fractions
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-d20b4a6c9ecd497384027e92240e0851
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Linked notes

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