Reaction #49571

Reaction equation

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

N-ethyl-1-propylamine

acetic acid

sodium triacetoxyborohydride

→

4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(N-ethyl-1-propylaminomethyl)indol-2-yl]isoindolinone

Yield 60.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=6/1)

Procedure

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (100 mg, 0.200 mmol) was dissolved in acetonitrile (5.8 mL), and the solution was treated with N-ethyl-1-propylamine (0.242 mL, 2.00 mmol), acetic acid (0.229 mL, 4.00 mmol) and sodium triacetoxyborohydride (253 mg, 1.19 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=6/1) to obtain 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(N-ethyl-1-propylaminomethyl)indol-2-yl]isoindolinone (68.4 mg, yield 60%).

Source