تفاعل #83697

معادلة التفاعل

2-methoxyphenylmagnesium bromide

(3aRS,5RS,7aSR)-2-benzyl-5-methyl-4-perhydroisoindolone

ammonium chloride

→

(3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-5methyl-4-perhydroisoindolol

المردود 98.9%

المذيبات

ethyl acetate

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONis added dropwise, at room temperature
2. 2
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 48 hours
3. 3
   غسيلwashed with saturated aqueous sodium chloride solution
4. 4
   أخرىThe organic phase is separated out after settling
5. 5
   تجفيفdried over magnesium sulphate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated to dryness under reduced pressure (2.7 kPa)
8. 8
   أخرىThe residue is chromatographed on a column of Merck silica gel (particle size 0.04-0.06 mm, diameter 2 cm, height 15 cm)
9. 9
   غسيلeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60/40 by volume)
10. 10
    أخرىcollecting 25 cm3 fractions
11. 11
    تركيزconcentrated to dryness under reduced pressure (2.5 kPa)

الإجراء التجريبي

To a suspension of 2.13 g of 2-methoxyphenylmagnesium bromide in 15 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 0.7 g of (3aRS,5RS,7aSR)-2-benzyl-5-methyl-4-perhydroisoindolone in 15 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 48 hours, treated with 50 cm3 of saturated aqueous ammonium chloride solution, taken up in ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase is separated out after settling has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of Merck silica gel (particle size 0.04-0.06 mm, diameter 2 cm, height 15 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60/40 by volume) and collecting 25 cm3 fractions. Fractions 10 to 20 are combined and then concentrated to dryness under reduced pressure (2.5 kPa). 1 g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-5methyl-4-perhydroisoindolol is obtained in the form of a yellow oil.

المصدر