Vinyl chloroformate → HCID 67915896, compound

HRID 1029949Notes

Reaction equation

HRID 1029949 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=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:20]1([CH3:24])[CH:21]=[CH:22][CH:23]=[C:18]([C:11]2([C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=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:19]=1

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 67915812HCID 67915812, compound

Product 1

HCID 67915896HCID 67915896, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (3aRS,7aRS)-2-benzyl-7,7-bis-(3-tolyl)-4-perhydroisoindolone (13.7 g) in 1,2-dichloroethane (150 cc) is treated with vinyl chloroformate (3.7 cc) and the mixture is refluxed for 3 hours and then concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on silica gel (particle size 0.04-0.063 mm, column 5.4 cm in diameter and 39 cm high), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80/20). Fractions 23 to 39 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-7,7-bis-(3-tolyl)-2-vinyloxycarbonyl-4-perhydroisoindolone (7.4 g) in the form of a white meringue.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. concentrationconcentrated under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on silica gel (particle size 0.04-0.063 mm, column 5.4 cm in diameter and 39 cm high)
  4. washeluting under a nitrogen pressure of 0.5 bar
  5. additionwith a mixture of cyclohexane and ethyl acetate (80/20)
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-61dc41efafff40e68e27c5b3e0c30522
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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