Reaction #74433

Reaction equation

(1R,4R,5S)-5-(tert-butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-one

L-Selectride

→

title compound

(1R,2R,4R,5S)-5-(tert-Butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-ol

Solvents

THF

Conditions

Workup

1. 1
   Otherquenched with tris-HCl (1M, PH 7.0 at 25° C.)
2. 2
   TemperatureThe mixture was warmed to ambient temp.
3. 3
   Otherpartitioned between EtOAc and Tris-HCl
4. 4
   WashThe combined organic portions were washed with brine
5. 5
   workup.DISSOLUTIONThe residue was dissolved in MeOH (60 mL)
6. 6
   workup.STIRRINGstirred with NaOH (pellets, 3.2 g) at 60° C. overnight
7. 7
   TemperatureAfter cooling to ambient temp.
8. 8
   Otherthe solvent was removed in vacuo
9. 9
   OtherThe residue was partitioned between diethyl ether and water
10. 10
    WashThe combined organic portions were washed with brine
11. 11
    Dryingdried with Na2SO4
12. 12
    Filtrationfiltered
13. 13
    OtherThe crude product was purified by flash column chromatography (0 to 30% of EtOAc in hexanes)

Procedure

To a solution of (1R,4R,5S)-5-(tert-butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-one (5.75 g, 15.8 mmol) in THF (15.0 mL) was added dropwise to L-Selectride (1.0 M solution in THF, 31.5 ml, 31.5 mmol) at −78° C. under nitrogen. The resulting mixture was stirred at −78° C. for 3 h, then quenched with tris-HCl (1M, PH 7.0 at 25° C.). The mixture was warmed to ambient temp. and partitioned between EtOAc and Tris-HCl. The combined organic portions were washed with brine, and conc. in vacuo. The residue was dissolved in MeOH (60 mL), stirred with NaOH (pellets, 3.2 g) at 60° C. overnight. After cooling to ambient temp., the solvent was removed in vacuo. The residue was partitioned between diethyl ether and water. The combined organic portions were washed with brine, dried with Na2SO4, filtered, and conc. in vacuo. The crude product was purified by flash column chromatography (0 to 30% of EtOAc in hexanes) to yield the title compound as a colorless oil.

Source