Reaktion #527020

Reaktionsgleichung

sodium hydroxide

5,10-Dihydro-8-methoxyindeno[1,2-b]indole

sodium cyanoborohydride

→

title compound

cis-4b,5,9b,10-Tetrahydro-8-methoxyindeno[1,2-b]indole

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe colourless reaction mixture was extracted into diethylether
2. 2
   Trocknenthe organic layers, dried (Na2SO4)
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigechromatographed (10% ethyl acetate/petrol 60°-80° C.)

Vorschrift

5,10-Dihydro-8-methoxyindeno[1,2-b]indole (770 mg, 3.3 mmol) was reacted with sodium cyanoborohydride (1.0 g, 16 mmol), in glacial acetic acid (17 cm3) solution. After 30 minutes, the solution was poured into ice/water, stirred for 1 hour, and neutralised with sodium hydroxide. The colourless reaction mixture was extracted into diethylether, the organic layers, dried (Na2SO4), and concentrated in vacuo. The residue was column chromatographed (10% ethyl acetate/petrol 60°-80° C.) to yield the title compound as a colourless solid. Yield: 520 mg (66%). M.p. 101° C. 1H NMR (CDCl3) δ: 3.28 (1H, dd,), 3.57 (1H, dd,), 3.80 (3H, s,), 3.85 (1H, br,), 4.24 (1H, dd,), 5.30 (1H, d,), 6.6-7.4 (7H, m,).

Quelle