2-Cyclohexen-1-one, 4,4-diphenyl- → (3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

HRID 1196255Notes

Reaction equation

HRID 1196255 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([N:27]1[CH:31]=[C-]O[C:28]1=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH2:20]([N:27]1[CH2:31][CH:11]2[CH:12]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][C:10]2=[O:13])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 1382802-Cyclohexen-1-one, 4,4-diphenyl-HCID 131717360HCID 131717360, compound

Product 1

HCID 19384608(3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindoloneYield 16.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4,4-diphenyl-2-cyclohexen-1-one (25 g) and 3-benzyl-5-oxazolidone (2.5 g) in dry toluene (100 cc) is heated to reflux for 2 hours 30 minutes. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063 mm, diameter 4.5 cm, height 23 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80:20 by volume) and collecting 50-cc fractions. Fractions 13 to 17 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-2-benzyl-7,7-diphenylperhydro-4-isoindolone (0.9 g) in the form of white crystals, m.p. 132° C.

Workup

  1. temperatureto reflux for 2 hours 30 minutes
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a column of silica gel (0.2-0.063 mm, diameter 4.5 cm, height 23 cm)
  4. washeluting under a nitrogen pressure of 0.5 bar
  5. additionwith a mixture of cyclohexane and ethyl acetate (80:20 by volume)
  6. customcollecting 50-cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-7137cb4722c146e387bcc962c30c5b21
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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