Reaktion #49562

Reaktionsgleichung

methylamine hydrochloride

triethylamine

acetic acid

sodium triacetoxyborohydride

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

→

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

Ausbeute 31.1%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by purification by flash column chromatography (chloroform/methanol=85/15)

Vorschrift

In a similar manner to Step 2 of Example 6, 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.494 g, 1.17 mmol) was dissolved in acetonitrile (16.0 mL), and the solution was treated with methylamine hydrochloride (1.60 mL, 23.4 mmol), triethylamine (3.30 mL, 23.4 mmol), acetic acid (1.30 mL, 23.4 mmol) and sodium triacetoxyborohydride (0.744 g, 3.51 mmol), followed by purification by flash column chromatography (chloroform/methanol=85/15) to obtain 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(methylaminomethyl)indol-2-yl]isoindolinone (0.159 g, 31%).

Quelle