Perfluoro-1-butanesulfonyl fluoride → 11beta-Fluorooestr-4-ene-3,17-dione

HRID 650343Notes

Reaction equation

HRID 650343 reaction equation
F[C:2]([F:17])(S(F)(=O)=O)[C:3](F)(F)[C:4](F)(F)[C:5](F)(F)F.O[C@@H]1C[C@@]2(C)[C@@H:30]([CH2:31][CH2:32][C:33]2=[O:37])[C@H:29]2[C@H:20]1[C@@H:21]1[C:26]([CH2:27][CH2:28]2)=[CH:25][C:24](=[O:38])[CH2:23][CH2:22]1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:17][C@H:2]1[CH2:3][C@@:4]2([CH3:5])[C@@H:30]([CH2:31][CH2:32][C:33]2=[O:37])[C@H:29]2[C@H:20]1[C@@H:21]1[C:26]([CH2:27][CH2:28]2)=[CH:25][C:24](=[O:38])[CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1090229811a-Hydroxy-estr-4-ene-3,17-dione

Product 1

HCID 1097914511beta-Fluorooestr-4-ene-3,17-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.6 ml of perfluorobutane-1-sulfonic acid fluoride is added in drops to 5.0 g of 11α-hydroxy-estr-4-ene-3,17-dione in 100 ml of toluene and 7.3 mnl of 1,8-diazabicyclo[5,4,0]undec-7-ene at 20° C. After 30 minutes, the solution is diluted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, 3.8 g of 11β-fluoro-estr-4-ene-3,17-dione with a melting point of 173-174° C. is obtained.

Workup

  1. washwashed with saturated sodium chloride solution
  2. customdried
  3. concentrationconcentrated by evaporation in a vacuum
  4. customAfter the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, 3.8 g of 11β-fluoro-estr-4-ene-3,17-dione with a melting point of 173-174° C.
  5. customis obtained

Sources & evidence

ORD record
ord-e5ce84d75dc34f11b217ec00c709d3f7
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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