Reaction #74384

Reaction equation

H2O2

NaOH

(1R,4R)-5,5-difluorobicyclo[2.2.1]heptan-2-one

L-Selectride

→

title compound

(1R,2R,4R)-5,5-Difluorobicyclo[2.2.1]heptan-2-ol

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe mixture was warmed to r.t.
2. 2
   workup.STIRRINGstirred at 65° C. for 10 h
3. 3
   TemperatureAfter cooling to ambient temperature
4. 4
   Extractionthe mixture was extracted with EtOAc (50 mL×2)
5. 5
   WashThe combined organic portions were washed with brine

Procedure

To a solution of (1R,4R)-5,5-difluorobicyclo[2.2.1]heptan-2-one (0.540 g, 3.7 mmol) in anhydrous tetrahydrofuran (8.00 mL) at −78° C. under nitrogen was added drop-wise L-Selectride (1.0 M solution in tetrahydrofuran, 7.40 mL). After stirring at −78° C. for 3 h, 30% H2O2 (6.0 mL) and 10% NaOH (aq., 10.0 mL) were added. The mixture was warmed to r.t. and then stirred at 65° C. for 10 h. After cooling to ambient temperature, the mixture was extracted with EtOAc (50 mL×2). The combined organic portions were washed with brine, and conc. in vacuo. Flash column chromatography (0 to 30% of ethyl acetate in hexanes) gave the title compound as a white solid.

Source