Reaktion #49595

Reaktionsgleichung

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

dimethylamine THF

acetic acid

sodium triacetoxyborohydride

→

4-chloro-5-[3-(tert-butyldimethylsiloxy)propyloxy]-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone

Ausbeute 83.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1)

Vorschrift

In a similar manner to Step 2 of Example 6, 4-chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (74.9 mg, 0.125 mmol) was dissolved in acetonitrile (2.5 mL), and the solution was treated with 2.0 mol/L dimethylamine-THF solution (0.63 mL, 1.25 mmol), acetic acid (0.072 mL, 1.25 mmol) and sodium triacetoxyborohydride (76.5 mg, 0.375 mmol), followed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1) to obtain 4-chloro-5-[3-(tert-butyldimethylsiloxy)propyloxy]-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone (65.0 mg, yield 83%).

Quelle