Hydrochloric Acid → 4,4-Dimethyl-6alpha-hydroxymethyl-17beta-hydroxyandrostan-3,7-dione

HRID 1182876Notes

Reaction equation

HRID 1182876 reaction equation
C1CO[C:3]2([CH2:20][CH2:19][C@@:18]3([CH3:21])[CH:5]([C@@H:6]([CH2:31][OH:32])[C:7](=[O:30])[C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C@@H:12]3[O:22][Si](C(C)(C)C)(C)C)[C:4]2([CH3:34])[CH3:33])[O:2]1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:33][C:4]1([CH3:34])[C:3](=[O:2])[CH2:20][CH2:19][C@@:18]2([CH3:21])[CH:5]1[C@@H:6]([CH2:31][OH:32])[C:7](=[O:30])[C@@H:8]1[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]1[CH2:10][CH2:11][C@@H:12]2[OH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 687291313,3-(Ethylenedioxy)-4,4-dimethyl-6alpha-hydroxymethyl-17beta-tert-butyl-dimethylsilyloxyandrostan-7-one

Product 1

HCID 687307524,4-Dimethyl-6alpha-hydroxymethyl-17beta-hydroxyandrostan-3,7-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,3-(ethylenedioxy)-4,4-dimethyl-6α-hydroxymethyl-17β-tert-butyl-dimethylsilyloxyandrostan-7-one (100 mg) was dissolved in dioxane (2 ml) then 1N HCl (2 ml) was added and the mixture stirred at RT for 5.5 h. 5% NaHCO3 was added and the solvent evaporated to dryness. The water phase was extracted with DCM, dried over Na2SO4 and evaporated to dryness to give 4,4-dimethyl-6α-hydroxymethyl-17β-hydroxyandrostan-3,7-dione in 95% yield.

Workup

  1. customthe solvent evaporated to dryness
  2. extractionThe water phase was extracted with DCM
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5f03c74621cf485faaf136a48fba4d01
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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