Reaction #70360

Reaction equation

LiAlH4

3β-hydroxy-5α,6α-epoxyandrostane-17-one

→

androstane-3β,5α,17β-triol

Yield 74.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   Temperatureat reflux for 8 h
2. 2
   TemperatureThe suspension was cooled with an ice bath
3. 3
   Otherquenched by careful addition of H2O (1 mL) and 4N NaOH (0.20 mL)
4. 4
   FiltrationThe mixture was filtered through a Celite pad
5. 5
   Washthe filter cake was washed with THF (3×10 mL)
6. 6
   DryingThe filtrate was dried over Na2SO4
7. 7
   Otherevaporated to dryness
8. 8
   Otherthe residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 40/30/30)

Procedure

To a stirred suspension of LiAlH4 (0.247 mg) in THF under N2 (10.5 mL), a solution of 3β-hydroxy-5α,6α-epoxyandrostane-17-one (0.64 g) in THF (20 mL) was added dropwise and the mixture was stirred at reflux for 8 h. The suspension was cooled with an ice bath and then quenched by careful addition of H2O (1 mL) and 4N NaOH (0.20 mL). The mixture was filtered through a Celite pad and the filter cake was washed with THF (3×10 mL). The filtrate was dried over Na2SO4, evaporated to dryness and the residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 40/30/30) to give androstane-3β,5α,17β-triol (0.48 g, 74%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.37 (1H, d), 4.19 (1H, d), 3.78 (1H, m), 3.62 (1H, s), 3.39 (1H, m), 1.87-0.80 (21H, m), 0.86 (3H, s), 0.59 (3H, s).

Source