反応 #45869

反応方程式

Dess-Martin reagent

2-Cyclopropyl-7-[(1S*,3R*)-3-hydroxycyclopentyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

sodium thiosulfate

sodium hydrogencarbonate

→

compound

収率 89.0%

2-Cyclopropyl-5-methyl-7-(3-oxocyclopentyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

収率 89.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度again cooled at 0° C.
2. 2
   workup.STIRRINGby further stirring for 10 minutes
3. 3
   抽出The solution was extracted three times with dichloromethane
4. 4
   洗浄washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他The insoluble matter was separated by filtration
7. 7
   その他the solvent was evaporated away
8. 8
   その他the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

実験手順

2-Cyclopropyl-7-[(1S*,3R*)-3-hydroxycyclopentyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-302) (50 mg, 0.14 mmol) was dissolved in dichloromethane (1 ml), and at 0° C., Dess-Martin reagent (118 mg, 0.28 mmol) was added. The solution was stirred at room temperature for 3 hours, then again cooled at 0° C., and aqueous saturated sodium thiosulfate solution and an aqueous saturated sodium hydrogencarbonate solution were added, followed by further stirring for 10 minutes. The solution was extracted three times with dichloromethane. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=3:1, v/v) to obtain the entitled compound (44 mg, 89%) as a white solid.

出典