Hydrochloric Acid → (3beta,20S)-pregn-5-ene-3,20-diol 20-acetate

HRID 1069052Notes

Reaction equation

HRID 1069052 reaction equation
[C:1]([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]([CH2:15][C@@H:16]([O:26]C(OCC)C)[CH2:17][CH2:18]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2].Cl.O.C(=O)([O-])O.[Na+]>CC(C)=O>[C:1]([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]([CH2:15][C@@H:16]([OH:26])[CH2:17][CH2:18]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 57200658(3beta,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate

Product 1

HCID 21969303(3beta,20S)-pregn-5-ene-3,20-diol 20-acetateYield 97.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

iv)—A solution of (3β,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate (66.1 g) in acetone (1330 ml) was treated with a 4 M aqueous solution of hydrochloric acid (13.2 ml). The reaction mixture was stirred for 45 minutes and subsequently poured into a mixture of water (3 l) and a saturated aqueous solution of sodium hydrogen carbonate (500 ml). The resulting precipitate was collected by filtration and then dissolved in dichloromethane. The filtrate was extracted with ethyl acetate. The dichloromethane and ethyl acetate solutions were washed with a saturated aqueous solution of sodium hydrogen carbonate and with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,20S)-pregn-5-ene-3,20-diol 20-acetate (compound 5a; 53.5 g), which was used in the following step without further purification.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutiondissolved in dichloromethane
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe dichloromethane and ethyl acetate solutions were washed with a saturated aqueous solution of sodium hydrogen carbonate and with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4ffeb5118bc49da9475dd673fd2669d
Source dataset
uspto-grants-2001_06
Patent number
US06251887B1

Reaction notes

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