Estrone → 17-Deoxyestradiol

HRID 720770Notes

Reaction equation

HRID 720770 reaction equation
[CH3:1][C@@:2]12[C:18](=O)[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.NN.[OH-].[K+]>C(O)COCCO.C(O)CCC>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:14]([CH2:13][CH2:12][C:11]4[CH:10]=[C:9]([OH:20])[CH:8]=[CH:7][C:6]=43)[C@@H:15]1[CH2:16][CH2:17][CH2:18]2

Participants

6

Reactant 3

HCID 5870EstroneHCID 9321HydrazineHCID 14797Potassium Hydroxide

Product 1

HCID 588817-DeoxyestradiolYield 97.5%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
50 °C

Procedure

Into a stirring suspension of estrone (8.1 g, 30 mmols) in 60 mL diethylene glycol, 20 mL 1-butanol and 2 mL hydrazine anhydrous (60 mmols) were added. The reaction mixture was heated under reflux for 1 hour to get clear solution. After cooling reaction mixture to 50 ° C., 5.04 g KOH pellets (90 mmols) were added and butanol was distilled. The reaction mixture was heated at 50° C. for 2 hours and then cooled to RT. On pouring in to ice (50 g), 20 mL 6N HCl was added and the reaction mixture stirred to give white solid product. The product was separated by filtration, washed with cold water and dried under vac. to give 7.5 g (90%) product. The product was purified on silica gel column eluted with CHCl3/MeOH 99:1. 1H NMR in CDCl3 confirmed the product as estra-1,3,5(10)-triene-3-ol.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customto get clear solution
  5. temperatureAfter cooling
  6. customreaction mixture to 50 ° C.
  7. distillationbutanol was distilled
  8. temperaturecooled to RT
  9. additionOn pouring in to ice (50 g), 20 mL 6N HCl
  10. additionwas added
  11. customto give white solid product
  12. customThe product was separated by filtration
  13. washwashed with cold water
  14. customdried under vac

Sources & evidence

ORD record
ord-648679e93ca34b40b19e8865384512eb
Source dataset
uspto-grants-2006_11
Patent number
US07135581B2

Reaction notes

Loading…