Potassium Carbonate → (3aRS,7SR,7aRS)-2-benzyl-7-methyl-7-phenyl-4-perhydroisoindolone

HRID 55417Notes

Reaction equation

HRID 55417 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1.C(O[CH2:20][N:21]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:22][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl.FC(F)(F)C(O)=O>[CH2:27]([N:21]1[CH2:22][CH:6]2[CH:7]([C:2]([CH3:1])([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:3][CH2:4][C:5]2=[O:8])[CH2:20]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3176754-Methyl-4-phenylcyclohex-2-en-1-oneHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine

Product 1

HCID 67714154(3aRS,7SR,7aRS)-2-benzyl-7-methyl-7-phenyl-4-perhydroisoindolone

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 14.5 g of 4-methyl-4-phenylcyclohex-2-enone and 24.45 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 65 cm3 of dichloromethane are added, at a temperature of 25° C., 3 drops of trifluoroacetic acid. The reaction mixture is stirred at this temperature for 30 minutes and then heated to reflux for 2 hours. After cooling, 10 g of potassium carbonate are added, the mixture is stirred for 15 minutes and the solution is then filtered through a sinter funnel and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 5 cm, height 39 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 100 cm3 fractions. Fractions 8 to 30 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 9 g of (3aRS,7SR,7aRS)-2-benzyl-7-methyl-7-phenyl-4-perhydroisoindolone are obtained in the form of a yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling
  4. stirringthe mixture is stirred for 15 minutes
  5. filtrationthe solution is then filtered through a sinter funnel
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 5 cm, height 39 cm)
  8. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (80/20 by volume)
  9. customcollecting 100 cm3 fractions
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-33c7e14550954230ad2839ed8b8525ec
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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