Lithium Bromide → 7alpha-(5-Acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

HRID 650330Notes

Reaction equation

HRID 650330 reaction equation
[Br-].[Li+].[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[C@H:23]([CH2:24][CH2:25][C:26](=[O:30])[CH:27]=2)[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][CH2:21]2)([CH3:19])[C:17](=[O:31])[CH2:16][CH2:15]1)(=[O:5])[CH3:4]>C(#N)C.[Cu](Br)Br>[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[CH:27]=[C:26]([OH:30])[CH:25]=[CH:24][C:23]=2[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][CH2:21]2)([CH3:19])[C:17](=[O:31])[CH2:16][CH2:15]1)(=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 15838157HCID 15838157, compound

Product 1

HCID 158381587alpha-(5-Acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-oneYield 73.8%

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 6342AcetonitrileSolvent

Procedure

17.8 g of lithium bromide and 92.83 g of copper(II) bromide are added to a solution of 82.3 g of 7α-(5-acetoxypentyl)4-estr-ene-3,17-dione in 936 ml of acetonitrile at a bath temperature of 80° C. After 10 minutes at a bath temperature of 80° C., the reaction solution is cooled, extracted three times with ethyl acetate, washed with water and sodium bicarbonate solution and dried. The residue that is obtained after the concentration by evaporation is chromatographed on silica gel, and 60.4 g of 7α-(5-acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained as oil.

Workup

  1. temperaturethe reaction solution is cooled
  2. extractionextracted three times with ethyl acetate
  3. washwashed with water and sodium bicarbonate solution
  4. customdried
  5. customThe residue that is obtained
  6. concentrationafter the concentration
  7. customby evaporation
  8. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-c1f178a5e75e42a68e8e6982775a6bfe
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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