HCID 68729052, compound → HCID 68733445, compound

HRID 1182886Notes

Reaction equation

HRID 1182886 reaction equation
[F:1][C@@H:2]1[CH2:19][C@@:18]2([CH3:20])[C:5]([C:6]([O:22]C)=[CH:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[OH:21])=[CH:4][C:3]1=[O:24]>C1COCC1.Cl>[F:1][C@@H:2]1[CH2:19][C@@:18]2([CH3:20])[C:5]([C:6](=[O:22])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[OH:21])=[CH:4][C:3]1=[O:24]

Participants

4

Reactant 1

HCID 68729052HCID 68729052, compound

Product 1

HCID 68733445HCID 68733445, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2α-fluoro-6-methoxy-17β-hydroxyandrosta-4,6-dien-3-one (610 mg) in THF (10 ml), 3N HCl (2 ml) was added and the mixture refluxed for 1 h. After cooling, Na2HPO4 5% was added and the reaction mixture was extracted with EtOAc. The organic phase was washed with H2O and brine, dried over Na2SO4 and evaporated to dryness. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/DCM/acetone 5/3/2) to give 2α-fluoro-17β-hydroxyandrost-4-en-3,6-dione (590 mg, 84% yield).

Workup

  1. temperaturethe mixture refluxed for 1 h
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe crude reaction mixture
  8. customwas purified by flash chromatography (SiO2, n-hexane/DCM/acetone 5/3/2)

Sources & evidence

ORD record
ord-3920c2c8b8db4e46a9dd945d0c856680
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

Loading…