Benzoyl Peroxide → 3alpha-Acetoxy-17alpha-bromo-5alpha-pregnan-20-one

HRID 2253813Notes

Reaction equation

HRID 2253813 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[Br:27]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@:14]2([Br:27])[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53835422Allopregnan-3alpha-ol-20-one acetate

Product 1

HCID 700849853alpha-Acetoxy-17alpha-bromo-5alpha-pregnan-20-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3α-Acetoxy-5α-pregnan-20-one (3 g, 360.5 g/m, 8.3 mmol), N-bromosuccinimide (2.7 g, 178 g/m, 15 mmol), and benzoyl peroxide (200 mg, 242 g/m, 0.83 mmol) dissolved in 50 ml of carbon tetrachloride were refluxed overnight (ca. 16h). The reaction mixture was cooled, filtered, and washed with sodium bisulfite, water, and brine, and then concentrated to give a crude reddish oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washwashed with sodium bisulfite, water, and brine
  4. concentrationconcentrated
  5. customto give a crude reddish oil

Sources & evidence

ORD record
ord-ac6f6f915a4e48b9a72a6154ed527243
Source dataset
uspto-grants-1993_08
Patent number
US05232917

Reaction notes

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