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

HRID 1599129Notes

Reaction equation

HRID 1599129 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+]>FC(F)(F)C(O)=O.ClCCl>[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-perhydroisoindoloneYield 70.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

Two drops of trifluoroacetic acid are added to a solution of 6.5 g of 5-acetoxymethylcyclohex-2-en-1-one and 14 g of N-butoxymethyl-N-trimethylsilylmethylbenzylamine [prepared according to the method described by Y. Tarao et al., Chem. Pharm. Bull., 33., 2762 (1985)] in 60 cm3 of dry dichloromethane. On reaching reflux, the reaction mixture is maintained at the same temperature for 30 minutes and 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 silica gel column (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-benzylperhydroisoindol-4-one are obtained in the form of a yellowish oil.

Workup

  1. customprepared
  2. temperatureOn reaching reflux
  3. temperaturethe reaction mixture is maintained at the same temperature for 30 minutes
  4. customthe suspension obtained
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe oily residue obtained
  8. customis chromatographed on a silica gel column (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-206eec31bed04729a07e37373d042e87
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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