Reacción #45871

Ecuación de reacción

6-[3-(tert-Butyldimethylsiloxy)cyclopent-1-enyl]-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

tetra-n-butylammonium fluoride

ammonium chloride

→

compound

Rendimiento 46.0%

2-Cyclopropyl-7-fluoro-6-(3-hydroxycyclopent-1-enyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

Rendimiento 46.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGby stirring at the same temperature for 5 minutes
2. 2
   ExtracciónThis was extracted three times with ethyl acetate
3. 3
   Lavadowashed with saturated brine
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   OtroThe insoluble matter was separated by filtration
6. 6
   Otrothe solvent was evaporated away
7. 7
   Otrothe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Procedimiento

6-[3-(tert-Butyldimethylsiloxy)cyclopent-1-enyl]-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-304) (275 mg, 0.67 mmol) was dissolved in tetrahydrofuran (6 ml), and at 0° C., tetra-n-butylammonium fluoride (1.0 M tetrahydrofuran solution, 1.0 ml, 1.0 mmol) was added. After stirring at room temperature under nitrogen atmosphere for 16 hours, aqueous saturated ammonium chloride solution was added to the solution at 0° C., followed by stirring at the same temperature for 5 minutes. This was extracted three times with ethyl acetate. 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=1:1, v/v) to obtain the entitled compound (91 mg, 46%) as a white solid.

Fuente