تفاعل #83690

معادلة التفاعل

potassium carbonate

6-acetoxy-4,4-dimethylcyclohex-2-enone

trifluoroacetic acid

N-butoxymethyl-N-trimethylsilylmethylbenzylamine

→

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

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   ترشيحthe solution is filtered through a sinter funnel
2. 2
   تركيزconcentrated to dryness under reduced pressure (2.7 kPa)
3. 3
   أخرىThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 8 cm, height 53 cm)
4. 4
   غسيلeluting under a pressure of 0.5 bar of nitrogen with a mixture of ethyl acetate and cyclohexane (20/80 by volume)
5. 5
   أخرىcollecting 250 cm3 fractions
6. 6
   تركيزconcentrated to dryness under reduced pressure (2.7 kPa)

الإجراء التجريبي

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.

المصدر