Reaction #56618

ord-f78aff742ae6442abb61a8b011739026

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
C[O-].[Na+]
sodium methanolate
→
C[C@]12CC[C@@H]3c4cc(I)c(O)cc4C[C@H](O)[C@H]3[C@@H]1CCC2=O
colorless crystals
Yield 68.6%
C[C@]12CC[C@@H]3c4cc(I)c(O)cc4C[C@H](O)[C@H]3[C@@H]1CCC2=O
3,7β-Dihydroxy-2-iodo-estra-1,3,5(10)-trien-17-one
Yield 68.6%

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
C[O-].[Na+]
sodium methanolate

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONThen, it was mixed with 2.5 g of Amberlite IR-120
  2. 2
    workup.STIRRINGstirred for 30 minutes
  3. 3
    Filtrationfiltered
  4. 4
    Concentrationthe solution was concentrated by evaporation in a rotary evaporator

Procedure

For the removal of both acetyl protective groups, 700 mg (1.4 mmol) of 3,7β-diacetoxy-2-iodo-estra-1,3,5(10)-trien-17-one, dissolved in 20 ml of methanol, was mixed with 200 mg of sodium methanolate, and the solution was stirred overnight. Then, it was mixed with 2.5 g of Amberlite IR-120, stirred for 30 minutes, filtered, and the solution was concentrated by evaporation in a rotary evaporator. Flash chromatography (cyclohexane/ethyl acetate) yielded 396 mg (68%) of colorless crystals.

Source

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