Pyridine → (3beta,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate

HRID 1385616Notes

Reaction equation

HRID 1385616 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@@H:17]([OH:19])[CH3:18])[CH2:8]1)[CH3:5])[CH3:2].N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>O>[C:35]([O:19][C@H:17]([C@@H:16]1[C@:20]2([CH3:28])[C@H:13]([C@H:12]3[C@H:23]([CH2:22][CH2:21]2)[C@:24]2([CH3:27])[C:9]([CH2:8][C@@H:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])[CH2:26][CH2:25]2)=[CH:10][CH2:11]3)[CH2:14][CH2:15]1)[CH3:18])(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54499381(3beta,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol

Product 1

HCID 57200658(3beta,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

iii)—A solution of (3β,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol (56.9 g) in a mixture of dry pyridine (144 ml) and acetic anhydride (72.4 ml) was stirred at room temperature for 18 h. Water (482 ml) was added and stirring was continued for another 1 h. The product was extracted into ethyl acetate; the combined organic phases 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)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate (compound 4; 66.1 g) which was used in the following step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for another 1 h
  3. extractionThe product was extracted into ethyl acetate
  4. washthe combined organic phases 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-055ad6fdf43a4861955256da6e0d645c
Source dataset
uspto-grants-2001_07
Patent number
US06262282B1

Reaction notes

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