Reacción #10260

Ecuación de reacción

Diisobutylaluminum hydride

ester

(3R,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexanecarboxylic Acid Methyl Ester

→

diol

Rendimiento 24.0%

[(3R,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexyl]methanol

Rendimiento 24.0%

Disolventes

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by the slow addition of 2N potassium sodium tartrate
2. 2
   TemperaturaThe solution was warmed to room temperature
3. 3
   workup.STIRRINGstirred for 15 min
4. 4
   workup.ADDITIONpoured into brine
5. 5
   Extracciónextracted with ethyl acetate and ether
6. 6
   Lavadowashed
7. 7
   workup.ADDITIONwith diluted (ca. 1%) HCl, and brine
8. 8
   Secadodried (MgSO4)
9. 9
   Otroevaporated
10. 10
    OtroThe crystalline residue was purified by flash chromatography
11. 11
    LavadoElution with hexane/ethyl acetate (9:1)

Procedimiento

Diisobutylaluminum hydride (1.5 M in toluene, 2.0 mL, 3 mmol) was added to a solution of the ester 3 (215 mg, 0.5 mmol) in anhydrous ether (3 mL) at −78° C. under argon. The mixture was stirred at −78° C. for 3 h and at −24° C. for 1.5 h, diluted with ether (10 mL) and quenched by the slow addition of 2N potassium sodium tartrate. The solution was warmed to room temperature and stirred for 15 min, then poured into brine and extracted with ethyl acetate and ether. The organic extracts were combined, washed with diluted (ca. 1%) HCl, and brine, dried (MgSO4) and evaporated. The crystalline residue was purified by flash chromatography. Elution with hexane/ethyl acetate (9:1) gave crystalline diol 4 (43 mg, 24%).

Fuente