Reacción #45869

Ecuación de reacción

Dess-Martin reagent

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

sodium thiosulfate

sodium hydrogencarbonate

→

compound

Rendimiento 89.0%

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

Rendimiento 89.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente