Réaction #70404

Équation de réaction

3β-tert-butyldimethylsilyloxyandrostane-6,17-dione

→

3β-hydroxyandrostane-6,17-dione

Rendement 86.0%

Solvants

EtOH

HCl

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   AutreAfter 3 h the solution was quenched with 5% aqueous NaHCO3 to pH 7
3. 3
   AutreThe organic solvent was evaporated
4. 4
   Extractionthe aqueous phase was extracted with CH2Cl2 (4×350 mL)
5. 5
   LavageThe combined organic extracts were washed with saturated aqueous NH4Cl, brine, H2O
6. 6
   Séchagedried over Na2SO4
7. 7
   Autreevaporated to dryness
8. 8
   AutreThe residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 90/10)

Mode opératoire

To a stirred suspension of 3β-tert-butyldimethylsilyloxyandrostane-6,17-dione (2.00 g) in EtOH (20 mL), 37% HCl (40 μL) was added. After 3 h the solution was quenched with 5% aqueous NaHCO3 to pH 7. The organic solvent was evaporated and the aqueous phase was extracted with CH2Cl2 (4×350 mL). The combined organic extracts were washed with saturated aqueous NH4Cl, brine, H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 90/10) to give 3β-hydroxyandrostane-6,17-dione (1.25 g, 86%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.56 (1H, d), 3.31 (1H, m), 2.45-1.15 (20H, m), 0.77 (3H, s), 0.65 (3H, s).

Source