Potassium Carbonate → (3aRS,6SR,7aSR)-6-acetoxymethyl-2-benzyl-4-perhydroisoindolone

HRID 55423Notes

Reaction equation

HRID 55423 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH2:11][C:10](=[O:12])[CH:9]=[CH:8][CH2:7]1)(=[O:3])[CH3:2].C(O[CH2:18][N:19]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:20][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl.FC(F)(F)C(O)=O>[C:1]([O:4][CH2:5][CH:6]1[CH2:7][CH:8]2[CH:9]([CH2:18][N:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:20]2)[C:10](=[O:12])[CH2:11]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamineHCID 140390975-Acetoxymethyl-2-cyclohexen-1-one

Product 1

HCID 18931543(3aRS,6SR,7aSR)-6-acetoxymethyl-2-benzyl-4-perhydroisoindolone

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.5 g of 5-acetoxymethyl-2-cyclohexen-1-one [J. Am. Chem. Soc., 110, 2919 (1988)]and 14 g of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 60 cm3 of dry dichloromethane are added 2 drops of trifluoroacetic acid. The reaction mixture reaches reflux and is maintained at the same temperature for 30 minutes and is then left at 20° C. for one hour. After addition of 1.0 g of potassium carbonate, the suspension obtained is filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The oily residue obtained is chromatographed on a column of silica gel (particle size 0.06-0.2 mm, height 42 cm) in a mixture of cyclohexane and ethyl acetate (40/60 by volume) and then in ethyl acetate. 8.2 g of (3aRS,6SR,7aSR)-6-acetoxymethyl-2-benzyl-4-perhydroisoindolone are obtained in the form of a yellowish oil.

Workup

  1. temperatureThe reaction mixture reaches reflux
  2. temperatureis maintained at the same temperature for 30 minutes
  3. customthe suspension obtained
  4. filtrationis filtered
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe oily residue obtained
  7. customis chromatographed on a column of silica gel (particle size 0.06-0.2 mm, height 42 cm) in a mixture of cyclohexane and ethyl acetate (40/60 by volume)

Sources & evidence

ORD record
ord-cd8420a7d1704a24b39b75b7460851ed
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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