Trifluoroacetic acid → (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindolone

HRID 55412Notes

Reaction equation

HRID 55412 reaction equation
[C:1]([O:4][CH:5]1[C:10](=[O:11])[CH:9]=[CH:8][C:7]([CH3:13])([CH3:12])[CH2:6]1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C(O[CH2:26][N:27]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:28][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([O:4][CH:5]1[CH2:6][C:7]([CH3:13])([CH3:12])[CH:8]2[CH:9]([CH2:26][N:27]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:28]2)[C:10]1=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamineHCID 133802996-Acetoxy-4,4-dimethylcyclohex-2-enone

Product 1

HCID 67714110(3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 23.2 g of 6-acetoxy-4,4-dimethylcyclohex-2-enone and 0.8 cm3 of trifluoroacetic acid in 770 cm3 of dichloromethane are added, at room temperature, 43 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine. The reaction mixture is stirred at room temperature for 15 hours then 5 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 8 cm, height 53 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of ethyl acetate and cyclohexane (20/80 by volume) and collecting 250 cm3 fractions. Fractions 18 to 27 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 6.6 g of (3aRS,5RS,7aRS)-5 -acetoxy-2-benzyl-7,7-dimethyl-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 8 cm, height 53 cm)
  4. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of ethyl acetate and cyclohexane (20/80 by volume)
  5. customcollecting 250 cm3 fractions
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-f22f57adc3ee43448a1ab5fbe2bbde93
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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