2,3,5-Triiodobenzoic acid → 5-Androstene-3 beta,7 beta,17 beta-triol

HRID 1197729Notes

Reaction equation

HRID 1197729 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[O:28])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24]C(=O)C)[CH2:6]1)(=O)C.[O-]S([O-])(=O)=O.[Mg+2].C1C(I)=C(I)C(C(O)=O)=CC=1I>CCCCC>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C@H:9]([OH:28])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[OH:24])[CH2:6]1

Participants

5

Reactant 3

HCID 69482,3,5-Triiodobenzoic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 9886600(3S,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate

Product 1

HCID 98180245-Androstene-3 beta,7 beta,17 beta-triolYield 86%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A solution of 3β,17β diacetoxyandrost-5-en-7-one (0.9581 g, 2.466 mmol) and pentane (30 mL), dried over MgSO4) were mixed under a nitrogen atmosphere. TIBA (9.5 mL, 9.5 mmol, 1M in toluene) was then added dropwise by syringe. The solution was stirred at room temperature for about 1 hour. The reaction was terminated by the addition of diluted hydrochloric acid (approximately 5mL). This solution was added to water (100 mL) and extracted with ethyl acetate (3 times with 50 mL). The organic layers were combined and then washed several times with saturated sodium bicarbonate solution (50 ml), saturated sodium chloride solution (two times with 50 mL,) and water (50 mL). The organic layer was dried over magnesium sulfate and the solvent removed by rotary evaporation to yield 86% crude product. 1H NMR indicated that the crude product contained 3β,17β,-diacetoxy-7-β-hydroxyandrost-5-en-7-one (86%) and 3β,17β-diacetoxy- 7-α-hydroxyandrost-5-ene.

Workup

  1. additionwere mixed under a nitrogen atmosphere
  2. customThe reaction was terminated by the addition of diluted hydrochloric acid (approximately 5mL)
  3. additionThis solution was added to water (100 mL)
  4. extractionextracted with ethyl acetate (3 times with 50 mL)
  5. washwashed several times with saturated sodium bicarbonate solution (50 ml), saturated sodium chloride solution (two times with 50 mL,) and water (50 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-164313e04c6345e38430f66a352167e5
Source dataset
uspto-grants-1994_01
Patent number
US05277907

Reaction notes

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