Réaction #49402

Équation de réaction

4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

triphenylphosphine

benzylalcohol

DEAD toluene

→

4-benzyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Rendement 73.3%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autrefollowed by purification by flash column chromatography (chloroform/methanol=100/0 to 90/10)

Mode opératoire

In a similar manner to Step 1 of Example 149, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (80.0 mg, 0.173 mmol) was dissolved in THF (4.0 mL), and the solution was treated with triphenylphosphine (137 mg, 0.519 mmol), benzylalcohol (0.0534 mL, 0.519 mmol) and 40% DEAD-toluene solution (0.237 mL), followed by purification by flash column chromatography (chloroform/methanol=100/0 to 90/10) to obtain 4-benzyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (70 mg, yield 73%).

Source