Progesterone Impurity D → 20alpha-Dihydroprogesterone

HRID 1385619Notes

Reaction equation

HRID 1385619 reaction equation
C([O:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=O)C>O1CCCC1.CO.O>[OH:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6]

Participants

5

Reactant 1

HCID 57099835Progesterone Impurity D

Product 1

HCID 895620alpha-DihydroprogesteroneYield 224%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

—Potassium hydroxide (22.5 g) was added to a solution of (20S)-20-(acetyloxy)pregn-4-en-3-one (17.9 g) in tetrahydrofuran (418 ml), methanol (380 ml) and water (125 ml). The mixture was stirred for 3 h at room temperature and then poured into water (2 l). The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography afforded (20S)-20-hydroxypregn-4-en-3-one (compound 7; 35.4 g).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9de97f1ad9f9486bbf6e086ca54e39e8
Source dataset
uspto-grants-2001_07
Patent number
US06262282B1

Reaction notes

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