Diisopropyl Ether → (3aRS,7aRS)-7,7-Diphenyl-2-vinyloxycarbonylperhydro-4-isoindolone

HRID 1029870Notes

Reaction equation

HRID 1029870 reaction equation
Cl[C:2]([O:4][CH:5]=[CH2:6])=[O:3].C([N:14]1[CH2:22][CH:21]2[CH:16]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][CH2:19][C:20]2=[O:23])[CH2:15]1)C1C=CC=CC=1.C(OC(C)C)(C)C>ClCCCl>[C:30]1([C:17]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:16]3[CH:21]([CH2:22][N:14]([C:2]([O:4][CH:5]=[CH2:6])=[O:3])[CH2:15]3)[C:20](=[O:23])[CH2:19][CH2:18]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 78808Vinyl chloroformateHCID 19384608(3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

Product 1

HCID 67915936(3aRS,7aRS)-7,7-Diphenyl-2-vinyloxycarbonylperhydro-4-isoindolone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Vinyl chloroformate (56 cc) is added dropwise in the course of 10 minutes to a solution of (3aRS,7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone (193 g) in 1,2-dichloroethane (1,225 cc) cooled to +5° C. After stirring for 30 minutes at between 10° and 20° C., the reaction mixture is refluxed for 90 minutes, cooled and concentrated to dryness under reduced pressure (2.7 kPa then 1 kPa). The crystalline mass obtained is pounded with cold isopropyl ether (200 cc). The crystals obtained are drained, washed with isopropyl ether (2 * 100 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-vinyloxycarbonyl-4-perhydroisoindolone (177 g) melting at 178° C. is obtained.

Workup

  1. temperaturecooled to +5° C
  2. temperaturethe reaction mixture is refluxed for 90 minutes
  3. temperaturecooled
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa
  5. customThe crystalline mass obtained
  6. customThe crystals obtained
  7. washwashed with isopropyl ether (2 * 100 cc)
  8. customdried

Sources & evidence

ORD record
ord-81fb5b4ff28c45949907cc78d5c77050
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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