Vinyl chloroformate → (3aRS,7aRS)-7,7-bis(3-chlorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone

HRID 1029943Notes

Reaction equation

HRID 1029943 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)C1C=CC=CC=1.Cl[C:33]([O:35][CH:36]=[CH2:37])=[O:34]>ClCCCl.C(OC(C)C)(C)C>[Cl:31][C:27]1[CH:26]=[C:25]([C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH:10]3[CH:15]([CH2:16][N:8]([C:33]([O:35][CH:36]=[CH2:37])=[O:34])[CH2:9]3)[C:14](=[O:17])[CH2:13][CH2:12]2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 78808Vinyl chloroformateHCID 67915832HCID 67915832, compound

Product 1

HCID 67915885(3aRS,7aRS)-7,7-bis(3-chlorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A solution of (3aRS,7aRS)-2-benzyl-7,7-bis-(3-chlorophenyl)-4-perhydroisoindolone (11.5 g) in 1,2-dichloroethane (250 cc) is treated with vinyl chloroformate (2.8 cc) and refluxed for 16 hours and then concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 6 cm, height 32 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80/20) and collecting 25 cc fractions. Fractions 19 to 27 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The meringue obtained is solidified in isopropyl ether and the precipitate is drained, washed with isopropyl ether and dried to give (3aRS,7aRS)-7,7-bis-(3-chlorophenyl)-2-vinyloxycarbonyl-4-perhydroisoindolone (6.7 g) in the form of a white solid.

Workup

  1. temperaturerefluxed for 16 hours
  2. concentrationconcentrated under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 6 cm, height 32 cm)
  4. washeluting under a nitrogen pressure of 0.5 bar
  5. additionwith a mixture of cyclohexane and ethyl acetate (80/20)
  6. customcollecting 25 cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe meringue obtained
  9. washwashed with isopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-6441133e41cf45a68c720bda756c42db
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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