Reaktion #1884609

Reaktionsgleichung

36

(3S, 4S)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-[(dimethylphenylsilyl)methyl]-2-methylenecyclopentanone

lithium triethylborohydride

→

crude title compound

Ausbeute 95.0%

4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-[(dimethylphenylsilyl)methyl]-2-methylenecyclopentanol

Ausbeute 95.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with an argon inlet
2. 2
   Temperaturslowly warmed to room temperature
3. 3
   Sonstigethe reaction
4. 4
   SonstigeThe reaction mixture was quenched with sodium hydroxide solution (10%, 25 mL)
5. 5
   Extraktionextracted with ethyl acetate (2×25 mL)
6. 6
   SonstigeThe organic layer was separated
7. 7
   Waschenwashed with brine (50 mL)
8. 8
   Trocknendried over magnesium sulfate

Vorschrift

To a cooled (−78° C.), stirred solution of 36 (4.8 g, 12.81 mmol) in THF (25 mL) in a 100-mL round bottomed flask equipped with an argon inlet was added lithium triethylborohydride (super hydride®, 24.4 mL, 24.4 mmol, 1.0 M THF solution) over a period of 15 minutes. The reaction mixture was stirred at the same temperature for 1 hour and slowly warmed to room temperature to complete the reaction. The reaction mixture was quenched with sodium hydroxide solution (10%, 25 mL) and extracted with ethyl acetate (2×25 mL). The organic layer was separated, washed with brine (50 mL), and dried over magnesium sulfate. Concentration of the organic layer in vacuo gave the crude title compound, 4.58 g in 95% yield in a 8:1 diastereomeric ratio. The title compound was purified by using silica gel flash chromatography ethyl acetate/hexanes (1:4 v/v) to afford the desired diastereomer, 4 g in 83% yield.

Quelle