Reaction #527907

ord-b6cfd10e4ae540c99c4d52767e53deb8

Reaction equation

CCOC(CO[C@H]1CC[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)C4OCCOC4C[C@@H]32)C1)OCC
3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane
O=C(O)C(O)C(O)C(=O)O
tartaric acid
O
water
→
C[C@]12CC[C@H](OCC=O)CC1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-formylmethoxy-androstan-17-one
Yield 84.7%

Reactants

—
saturated solution
CCOC(CO[C@H]1CC[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)C4OCCOC4C[C@@H]32)C1)OCC
3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane
O=C(O)C(O)C(O)C(=O)O
tartaric acid
O
water

Reagents

None

Solvents

C1COCCO1
dioxane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwere then added
  2. 2
    Extractionthe residue was extracted with methylene chloride
  3. 3
    WashThe organic layer was washed with water
  4. 4
    Dryingdried over anhydrous sodium sulfate
  5. 5
    Otherevaporated to dryness under reduced pressure
  6. 6
    OtherThe crude product was purified by flash-chromatography (SiO2)

Procedure

A solution of 7.2 g of 3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane, in 250 ml of dioxane and 250 ml of a saturated solution of tartaric acid was heated at 70° C. for 2 hrs in a nitrogen atmosphere, 100 ml of water were then added and the residue was extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using as eluant n-hexane/ethyl acetate 70/30 to give 4.5 g of 3β-formylmethoxy-androstan-17-one as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05521167uspto-grants-1996_05