Reaktion #74433

Reaktionsgleichung

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

L-Selectride

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title compound

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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