Reaction #49377

Reaction equation

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

triphenylphosphine

tert-butyl N-(3-hydroxypropyl)carbamate

DEAD toluene

→

(3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Yield 88.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=4/1)

Procedure

In a similar manner to Step 1 of Example 149, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (60.0 mg, 0.130 mmol) was dissolved in THF (3.6 mL), and the solution was treated with triphenylphosphine (136 mg, 0.78 mmol), tert-butyl N-(3-hydroxypropyl)carbamate (92 mg, 0.52 mmol) and 40% DEAD-toluene solution (0.236 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=4/1) to obtain 4-[(3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (70.5 mg, yield 88%).

Source