Vinyl chloroformate → HCID 67916103, compound

HRID 1196240Notes

Reaction equation

HRID 1196240 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]([F:31])[CH:26]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F: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>[F:31][C:27]1[CH:26]=[C:25]([C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F: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

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 67915874HCID 67915874, compound

Product 1

HCID 67916103HCID 67916103, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (3aRS,7aRS)-2-benzyl-7,7-bis(3-fluorophenyl)perhydro-4-isoindolone (92.2 g) in 1,2-dichloroethane (860 cc) is treated with vinyl chloroformate (26.3 cc) and heated to reflux for 3 hours, then concentrated under reduced pressure (2.7 kPa). The residue is chromatographed (in two runs) on silica gel (particle size 0.04-0.063 mm, columns 8 cm in diameter and 35 cm high), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (75:25). The meringue-like product obtained is crystallized in isopropyl ether to give (3aRS,7aRS)-7,7-bis(3-fluorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone (50.3 g). M.p. 152° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed (in two runs) on silica gel (particle size 0.04-0.063 mm, columns 8 cm in diameter and 35 cm high)
  5. washeluting under a nitrogen pressure of 0.5 bar
  6. additionwith a mixture of cyclohexane and ethyl acetate (75:25)
  7. customThe meringue-like product obtained
  8. customis crystallized in isopropyl ether

Sources & evidence

ORD record
ord-005f18bfc68c449585dfb280475964c9
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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