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

HRID 232800Notes

Reaction equation

HRID 232800 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-2999bd1f158645bab610f3e064a88394
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Reaction notes

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