Réaction #74433

Équation de réaction

(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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autrequenched with tris-HCl (1M, PH 7.0 at 25° C.)
2. 2
   TempératureThe mixture was warmed to ambient temp.
3. 3
   Autrepartitioned between EtOAc and Tris-HCl
4. 4
   LavageThe 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
   TempératureAfter cooling to ambient temp.
8. 8
   Autrethe solvent was removed in vacuo
9. 9
   AutreThe residue was partitioned between diethyl ether and water
10. 10
    LavageThe combined organic portions were washed with brine
11. 11
    Séchagedried with Na2SO4
12. 12
    Filtrationfiltered
13. 13
    AutreThe crude product was purified by flash column chromatography (0 to 30% of EtOAc in hexanes)

Mode opératoire

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