Reaktion #2368246

Reaktionsgleichung

water

1-(cyclopropylmethyl)-5-{4-[(3-methyl-2,4-dioxoimidazolidin-1-yl)methyl]phenyl}-1H-benzotriazole-4-carbaldehyde

1-(Cyclopropylmethyl)-5-{4-[(3-methyl-2,4-dioxoimidazolidin-1-yl)methyl]phenyl}-1H-benzotriazole-4-carbaldehyde

sodium borohydride

→

titled compound

1-{4-[1-(Cyclopropylmethyl)-4-(hydroxymethyl)-1H-benzotriazol-5-yl]benzyl}-3-methylimidazolidine-2,4-dione

Lösungsmittel

dichloromethane

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine
2. 2
   ExtraktionThe organic extract
3. 3
   Trocknenwas dried with magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified via silica gel chromatography (ethyl acetate/hexane gradient)

Vorschrift

To a solution of 1-(cyclopropylmethyl)-5-{4-[(3-methyl-2,4-dioxoimidazolidin-1-yl)methyl]phenyl}-1H-benzotriazole-4-carbaldehyde (Example 20, 72 mg, 0.18 mmol) in methanol (1.8 mL) was added sodium borohydride (6.8 mg, 0.18 mmol). After 1.5 hours, the mixture was treated with water, diluted with dichloromethane and washed with brine. The organic extract was dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound: 1H NMR (400 MHz, CDCl3) 7.54 (d, 1H, J=8.8 Hz), 7.42-7.45 (m, 3H), 7.35 (d, 2H, J=8.0 Hz), 5.12 (d, 2H, J=6.4 Hz), 4.65 (s, 2H), 4.55 (d, 2H, J=7.2 Hz), 3.83 (s, 2H), 3.08 (s, 3H), 1.40-1.47 (m, 1H), 0.67-0.71 (m, 2H), 0.51-0.55 (m, 2H) ppm. LRMS m/z (M+H) 406.0 found, 406.2 required.

Quelle