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

HRID 55403Notes

Reaction equation

HRID 55403 reaction equation
[C:1]([O:4][CH:5]1[C:10](=[O:11])[CH:9]=[CH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(O[CH2:17][N:18]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:19][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl.FC(F)(F)C(O)=O>[C:1]([O:4][CH:5]1[CH2:6][CH2:7][CH:8]2[CH:9]([CH2:17][N:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19]2)[C:10]1=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamineHCID 11389500ACETIC ACID 2-OXO-CYCLOHEX-3-ENYL ESTER

Product 1

HCID 67714196(3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindolone

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.5 g of 6-acetoxy-2-cyclohexenone and 16.83 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 150 cm3 of dichloromethane are added, at a temperature of 10° C., 12 drops of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 7 hours, then 2 g of potassium carbonate are 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 6 cm, height 35 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (97.5-2.5 by volume) and collecting 60 cm3 fractions. Fractions 25 to 39 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 6.25 g of (3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindolone are obtained in the form of a yellow oil.

Workup

  1. filtrationthe solution is filtered through a sinter funnel
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 6 cm, height 35 cm)
  4. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (97.5-2.5 by volume)
  5. customcollecting 60 cm3 fractions
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-b2578cec67144a53b41050292734757f
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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