Réaction #83705

Équation de réaction

sodium hydroxide

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

triethylamine

trifluoroacetic acid

→

perhydroisoindolone

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture, cooled to +5° C.
2. 2
   AutreThe organic phase is separated out
3. 3
   Lavagewashed with water
4. 4
   Séchagedried over magnesium sulphate
5. 5
   Concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
6. 6
   AutreThe oil obtained
7. 7
   Autreis crystallized in diisopropyl ether
8. 8
   LavageThe solid, washed with petroleum ether
9. 9
   Autredried under reduced pressure at 40° C

Mode opératoire

To a solution of 7 g of (3aRS,4RS,7aSR)-2-benzyl-7,7-dimethoxy -4-(2-methoxyphenyl)-4-perhydroisoindolol in 70 cm3 of dry dichloromethane are added 6.5 cm3 of triethylamine and 6.5 cm3 of trifluoroacetic acid. After stirring for 3 hours at room temperature, the reaction mixture, cooled to +5° C., is basified with 50 cm3 of 1N sodium hydroxide. The organic phase is separated out, washed with water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is crystallized in diisopropyl ether. The solid, washed with petroleum ether, is then drained and dried under reduced pressure at 40° C. 3.4 g of (3aRS,7RS,7aSR)-2-benzyl-7-hydroxy -7-(2-methoxyphenyl)-4)-perhydroisoindolone are obtained, in the form of a cream-coloured solid. M.p.=96C.

Source