反应 #45596

反应方程式

Triethylamine

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

2-[2-(benzyloxy)-1,1-dimethylethyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

收率 91.1%

2-[2-(Benzyloxy)-1,1-dimethylethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

收率 91.1%

溶剂

ethyl acetate

反应条件

后处理

1. 1
   温度After cooling
2. 2
   其他the reaction liquid
3. 3
   洗涤washed three times with saturated brine
4. 4
   干燥dried over anhydrous magnesium sulfate
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

实验过程

Triethylamine (222 μl, 1.59 mmol), (3S)-3-(dimethylamino)pyrrolidine (152 μl, 1.19 mmol) were added to a dimethyl sulfoxide (16.5 ml) solution of 2-[2-(benzyloxy)-1,1-dimethylethyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-66) (330 mg, 0.796 mmol), followed by stirring overnight at 90° C. After cooling, the reaction liquid was diluted with ethyl acetate, washed three times with saturated brine, then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain the entitled compound (369 mg, 91%) as a pale brown oil.

来源