تفاعل #45869

معادلة التفاعل

Dess-Martin reagent

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

sodium thiosulfate

sodium hydrogencarbonate

→

compound

المردود 89.0%

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

المردود 89.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةagain cooled at 0° C.
2. 2
   workup.STIRRINGby further stirring for 10 minutes
3. 3
   استخلاصThe solution was extracted three times with dichloromethane
4. 4
   غسيلwashed with saturated brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   أخرىThe insoluble matter was separated by filtration
7. 7
   أخرىthe solvent was evaporated away
8. 8
   أخرىthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

الإجراء التجريبي

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.

المصدر