Potassium Carbonate → (3aRS,5RS,7aSR)-2benzyl-5-methyl-4-perhydroisoindolone

HRID 55420Notes

Reaction equation

HRID 55420 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[CH:6]=[CH:5][CH2:4][CH2:3]1.C(O[CH2:14][N:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:16][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl.FC(F)(F)C(O)=O>[CH2:21]([N:15]1[CH2:16][CH:6]2[CH:5]([CH2:4][CH2:3][CH:2]([CH3:1])[C:7]2=[O:8])[CH2:14]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110623356-Methylcyclohex-2-en-1-oneHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine

Product 1

HCID 67714068(3aRS,5RS,7aSR)-2benzyl-5-methyl-4-perhydroisoindolone

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g of 6-methyl-cyclohex-2-enone in 15 cm3 of dichloromethane are added, at room temperature, 3 drops of trifluoroacetic acid, followed by 3.6 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine. The reaction mixture is brought to reflux, with stirring, for 3 hours. After cooling, potassium carbonate is added and the solution is 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 2 cm, height 20 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60/40 by volume) and collecting 25 cm3 fractions. Fractions 10 to 20 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 0.7 g of (3aRS,5RS,7aSR)-2benzyl-5-methyl-4-perhydroisoindolone is obtained in the form of a colourless oil.

Workup

  1. temperatureto reflux
  2. temperatureAfter cooling
  3. filtrationthe solution is filtered through a sinter funnel
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 2 cm, height 20 cm)
  6. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60/40 by volume)
  7. customcollecting 25 cm3 fractions
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-80fb12f97ff14f5788212c1da7a9b3bb
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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