Sodium Methoxide → 3,7beta-Dihydroxy-2-iodo-estra-1,3,5(10)-trien-17-one

HRID 28340Notes

Reaction equation

HRID 28340 reaction equation
C([O:4][C:5]1[C:22]([I:23])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:24])[CH2:13][CH2:12]4)[C@@H:9]([O:25]C(=O)C)[CH2:8][C:7]=2[CH:6]=1)(=O)C.C[O-].[Na+]>CO>[OH:4][C:5]1[C:22]([I:23])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:24])[CH2:13][CH2:12]4)[C@@H:9]([OH:25])[CH2:8][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 691050063,7beta-Diacetoxy-2-iodo-estra-1,3,5(10)-trien-17-one

Product 1

HCID 116112933,7beta-Dihydroxy-2-iodo-estra-1,3,5(10)-trien-17-oneYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. additionThen, it was mixed with 2.5 g of Amberlite IR-120
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. concentrationthe solution was concentrated by evaporation in a rotary evaporator

Sources & evidence

ORD record
ord-f78aff742ae6442abb61a8b011739026
Source dataset
uspto-grants-2008_09
Patent number
US07419972B2

Reaction notes

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