Réaction #1250118

Équation de réaction

sodium cyanoborate

(tert-Butyldimethylsilanyloxy)acetaldehyde

acetic acid

sodium bicarbonate

7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

→

7-[2-(tert-butyldimethylsilanyloxy)ethylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Rendement 92.1%

Solvants

ethyl acetate

methanol

Conditions de réaction

Traitement

1. 1
   SéchageAn organic layer was dried over anhydrous sodium sulfate
2. 2
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure
3. 3
   AutreThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1)

Mode opératoire

(tert-Butyldimethylsilanyloxy)acetaldehyde (93.9 μL, 0.493 mmol) and acetic acid (169 μL, 2.96 mmol) were added to a methanol solution (30 ml) that contained the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (150 mg, 0.493 mmol) prepared in step C of Example 1-1. The obtained solution was cooled to 0° C., and sodium cyanoborate (1M THF solution, 1.48 mL, 1.48 mmol) was then added thereto. The obtained mixture was stirred at a room temperature for 18 hours. The reaction solution was poured into a mixed solution of ethyl acetate and a saturated sodium bicarbonate aqueous solution. An organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1), so as to obtain 7-[2-(tert-butyldimethylsilanyloxy)ethylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (210 mg, 92%).

Source