3beta-Tert-butyldimethylsilyloxyandrostane-6,17-dione → 3beta-Hydroxy-5alpha-androstan-6,17-dione

HRID 42126Notes

Reaction equation

HRID 42126 reaction equation
[Si]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:11]([C:12](=[O:29])[CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1)(C(C)(C)C)(C)C>CCO.Cl>[OH:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:11]([C:12](=[O:29])[CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1

Participants

4

Reactant 1

HCID 690112643beta-Tert-butyldimethylsilyloxyandrostane-6,17-dione

Product 1

HCID 690126423beta-Hydroxy-5alpha-androstan-6,17-dioneYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

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).

Workup

  1. additionwas added
  2. customAfter 3 h the solution was quenched with 5% aqueous NaHCO3 to pH 7
  3. customThe organic solvent was evaporated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (4×350 mL)
  5. washThe combined organic extracts were washed with saturated aqueous NH4Cl, brine, H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 90/10)

Sources & evidence

ORD record
ord-93e77a45bb4b49b1b72bf2b48a65a742
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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