Reaktion #308140

Reaktionsgleichung

sodium borohydride

1

1,2,3,4-Tetrahydro-benzo[b]azepin-5-one

4-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-methyl-benzonitrile

E101

NH4Cl

→

title compound

Ausbeute 35.0%

(4-Aminomethyl-3-methyl-phenyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone

Ausbeute 35.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2 h
2. 2
   workup.STIRRINGThe mixture was stirred for 30 min
3. 3
   Filtrationthe solid was filtered off through Celite®
4. 4
   Filtrationfilter agent
5. 5
   Einengenthe filtrate concentrated in vacuo
6. 6
   workup.DISSOLUTIONThe residue was re-dissolved in EtOAc
7. 7
   SonstigeThe layers were partitioned
8. 8
   Extraktionthe aqueous layer was extracted further with chloroform
9. 9
   Sonstigedried
10. 10
    Einengenconcentrated in vacuo
11. 11
    SonstigeThe residue was purified by flash chromatography on silica gel through an isolute (eluant; 1% 35% ammonia:9% methanol:90% dichloro-methane)

Vorschrift

A solution of 4-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-methyl-benzonitrile from Example E101.1 (1.42 g, 4.0 mmol) in methanol (50 ml) at 0° C. was treated with cobalt(II) chloride hexahydrate (1.90 g, 8.0 mmol). The mixture was stirred for 15 min at room temperature then sodium borohydride (1.51 g, 40.0 mmol) was added portionwise. The reaction mixture was stirred for 2 h then saturated NH4Cl was added. The mixture was stirred for 30 min then the solid was filtered off through Celite® filter agent and the filtrate concentrated in vacuo. The residue was re-dissolved in EtOAc and saturated NaHCO3. The layers were partitioned and the aqueous layer was extracted further with chloroform. Organics were combined, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; 1% 35% ammonia:9% methanol:90% dichloro-methane) to yield the title compound (511 mg, 35%).

Quelle