Reaktion #45869

Reaktionsgleichung

Dess-Martin reagent

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

sodium thiosulfate

sodium hydrogencarbonate

→

compound

Ausbeute 89.0%

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

Ausbeute 89.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle