Hydrogen Peroxide → 1044942-90-6

HRID 852763Notes

Reaction equation

HRID 852763 reaction equation
[F:1][C:2]1([F:10])[CH2:7][C@H:6]2[CH2:8][C@@H:3]1[CH2:4][C:5]2=[O:9].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].OO.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1([F:10])[CH2:7][C@H:6]2[CH2:8][C@@H:3]1[CH2:4][C@H:5]2[OH:9]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 58929678HCID 58929678, compound

Product 1

HCID 589297281044942-90-6

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

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., 110.0 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.

Workup

  1. temperatureThe mixture was warmed to r.t.
  2. stirringstirred at 65° C. for 10 h
  3. temperatureAfter cooling to ambient temperature
  4. extractionthe mixture was extracted with EtOAc (50 mL×2)
  5. washThe combined organic portions were washed with brine

Sources & evidence

ORD record
ord-4bd4db1619b14fc2bd22166b668c4646
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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