تفاعل #83680

معادلة التفاعل

ammonium chloride

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

2-methoxyphenylmagnesium bromide

→

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

المردود 26.8%

المذيبات

tetrahydrofuran

—

ice

ethyl ether

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONare added dropwise, at room temperature
2. 2
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 3 hours
3. 3
   أخرىThe organic phase is separated out after settling
4. 4
   تجفيفdried over magnesium sulphate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated to dryness under reduced pressure (2.7 kPa)
7. 7
   أخرىThe residue is crystallized in 80 cm3 of petroleum ether
8. 8
   أخرىchromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 20 cm)
9. 9
   غسيلeluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (95/5 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 27.6 g of 2-methoxyphenylmagnesium bromide in 60 cm' of tetrahydrofuran are added dropwise, at room temperature and with stirring, a solution of 4.7 g of (3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindolone in 90 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 3 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution and taken up in 200 cm3 of ethyl ether and 100 g of ice. 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 crystallized in 80 cm3 of petroleum ether and then chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 20 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (95/5 by volume) and collecting 25 cm3 fractions. Fractions 14 to 21 are combined and then concentrated to dryness under reduced pressure (2.5 kPa). 1.55 g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 140° C.

المصدر