반응 #45603

반응 방정식

sodium carbonate

formaldehyde

2-tert-butyl-5-methyl-7-(3-methylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Sodium cyanoborohydride

acetic acid

→

compound

수율 88.0%

2-Tert-butyl-5-methyl-7-(3-dimethylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

수율 88.0%

용매

brine

methanol

반응 조건

후처리

1. 1
   추출this was extracted with ethyl acetate and chloroform
2. 2
   건조dried over anhydrous magnesium sulfate
3. 3
   농축concentrated under reduced pressure
4. 4
   기타The resulting residue was purified by silica gel column chromatography (chloroform:methanol=200:1)
5. 5
   기타again purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:1)

실험 절차

Aqueous 36% formaldehyde solution (205 μl, 2.75 mmol) was added to a methanol (4 ml) solution of 2-tert-butyl-5-methyl-7-(3-methylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-73) (103 mg, 275 μmol), followed by cooling at 0° C. Sodium cyanoborohydride (34.6 mg, 550 μmol) and acetic acid (40.9 μl, 715 μmol) were added, followed by stirring at room temperature for 20 minutes. Aqueous 10% sodium carbonate solution and saturated brine were added to the reaction liquid, and this was extracted with ethyl acetate and chloroform. The organic layers were combined, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=200:1), again purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:1) to obtain the entitled compound (94 mg, 88%) as a colorless solid.

출처