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

HRID 1196232Notes

Reaction equation

HRID 1196232 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, cooled to +5° C., of (3aRS,7aRS)-2-benzyl-7,7-diphenylperhydro-4-isoindolone (193 g) in 1,2-dichloroethane (1225 cc). After stirring for 30 minutes at between 10° and 20° C., the reaction mixture is heated to reflux for 90 minutes, cooled and concentrated to dryness under reduced pressure (2.7 kPa then 1 kPa). The crystalline mass obtained is stirred vigorously 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-vinyloxycarbonylperhydro-4-isoindolone (177 g), m.p. 178° C. is obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux 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-fb4d8ce5e2b04fd1addfd5c8b9ceaa30
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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