Reaction #56619

ord-022b672239c24da4b4aa20a12dc2b233

Reaction equation

CC(=O)Oc1cc2c(cc1I)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1[C@@H](OC(C)=O)C2
3,7β-diacetoxy-2-iodo-estra-1,3,5(10)-trien-17-one
O=C([O-])O.[Na+]
sodium bicarbonate
→
CC(=O)O[C@H]1Cc2cc(O)c(I)cc2[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
7β-Acetoxy-3-hydroxy-2-iodo-estra-1,3,5(10)-trien-17-one

Reactants

CC(=O)Oc1cc2c(cc1I)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1[C@@H](OC(C)=O)C2
3,7β-diacetoxy-2-iodo-estra-1,3,5(10)-trien-17-one
O=C([O-])O.[Na+]
sodium bicarbonate

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThen, it was filtered
  2. 2
    Concentrationthe solution was concentrated by evaporation in a rotary evaporator
  3. 3
    OtherFlash chromatography (cyclohexane/ethyl acetate) yielded 402 mg (63%) of colorless crytstals

Procedure

700 mg (1.4 mmol) of 3,7β-diacetoxy-2-iodo-estra-1,3,5(10)-trien-17-one was dissolved in 30 ml of methanol, mixed with 1.0 g of sodium bicarbonate, and the reaction mixture was stirred overnight. Then, it was filtered, and the solution was concentrated by evaporation in a rotary evaporator. Flash chromatography (cyclohexane/ethyl acetate) yielded 402 mg (63%) of colorless crytstals.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419972B2uspto-grants-2008_09