Reaction #49399

Reaction equation

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

triphenylphosphine

tert-butyl N-(3-hydroxypropyl)carbamate

DEAD toluene

→

4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Yield 99.1%

Solvents

THF

Conditions

Workup

1. 1
   Otherfollowed by purification by flash column chromatography (chloroform/methanol=100/0 to 95/5)

Procedure

In a similar manner to Step 1 of Example 149, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (150 mg, 0.382 mmol) was dissolved in THF (7.5 mL), and the solution was treated with triphenylphosphine (200 mg, 0.764 mmol), tert-butyl N-(3-hydroxypropyl)carbamate (134 mg, 0.764 mmol) and 40% DEAD-toluene solution (0.348 mL), followed by purification by flash column chromatography (chloroform/methanol=100/0 to 95/5) to obtain 4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (208 mg, yield 99%).

Source