Reaktion #83695

Reaktionsgleichung

4-methyl-4-phenylcyclohex-2-enone

N-butoxymethyl-N-trimethylsilylmethylbenzylamine

potassium carbonate

→

(3aRS,7SR,7aRS)-2-benzyl-7-methyl-7-phenyl-4-perhydroisoindolone

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for 2 hours
3. 3
   TemperaturAfter cooling
4. 4
   workup.STIRRINGthe mixture is stirred for 15 minutes
5. 5
   Filtrationthe solution is then filtered through a sinter funnel
6. 6
   Einengenconcentrated to dryness under reduced pressure (2.7 kPa)
7. 7
   SonstigeThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 5 cm, height 39 cm)
8. 8
   Wascheneluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (80/20 by volume)
9. 9
   Sonstigecollecting 100 cm3 fractions
10. 10
    Einengenconcentrated to dryness under reduced pressure (2.7 kPa)

Vorschrift

To a solution of 14.5 g of 4-methyl-4-phenylcyclohex-2-enone and 24.45 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 65 cm3 of dichloromethane are added, at a temperature of 25° C., 3 drops of trifluoroacetic acid. The reaction mixture is stirred at this temperature for 30 minutes and then heated to reflux for 2 hours. After cooling, 10 g of potassium carbonate are added, the mixture is stirred for 15 minutes and the solution is then 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 5 cm, height 39 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 100 cm3 fractions. Fractions 8 to 30 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 9 g of (3aRS,7SR,7aRS)-2-benzyl-7-methyl-7-phenyl-4-perhydroisoindolone are obtained in the form of a yellow oil.

Quelle