Réaction #69738

Équation de réaction

(2,4-bis-benzyloxy-5-isopropenyl-phenyl)-(4-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone

4-(3-chloropropyl)morpholine

caesium carbonate

→

(2,4-bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone

Rendement 71.5%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autrethen evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   Lavagewashed with brine
4. 4
   Séchagedried (MgSO4)
5. 5
   Autreevaporated
6. 6
   AutrePurification of the crude material
7. 7
   Lavageelution
8. 8
   Autreform 0% to 10% MeOH/EtOAc

Mode opératoire

A mixture of (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-(4-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone (2 g; 4.07 mmol), 4-(3-chloropropyl)morpholine (1.66 g; 2.5 equiv.) and caesium carbonate (8.3 g; 6.25 equiv) in DMF was heated at 90° C. overnight then evaporated. The residue was dissolved in EtOAc, washed with brine, dried (MgSO4) and evaporated. Purification of the crude material using a Biotage SP4 (40 S, 40 ml/min), using gradient elution form 0% to 10% MeOH/EtOAc gave 1.8 g of (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone as a pale yellow gum. MS: [M+H]+ 619.

Source