p-Toluenesulfonic acid → 7alpha-(5-Acetoxypentyl)-11beta-fluoro-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-one

HRID 1838883Notes

Reaction equation

HRID 1838883 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([OH:28])[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][C@@H:19]2[F:29])([CH3:17])[C:15](=[O:30])[CH2:14][CH2:13]1)(=[O:3])[CH3:2].[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([O:28][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][O:31]3)[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][C@@H:19]2[F:29])([CH3:17])[C:15](=[O:30])[CH2:14][CH2:13]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 699351197alpha-(5-Acetoxypentyl)-11beta-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one

Product 1

HCID 229418067alpha-(5-Acetoxypentyl)-11beta-fluoro-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.2 g of 7α-(5-acetoxypentyl)-11β-fluoro-3-hydroxyestra-1,3,5(10)-trien-17-one in 86 ml of THF are stirred at RT for 2.5 h with 8.6 ml of 3,4-dihydro-2H-pyran and 820 mg of p-toluenesulphonic acid. 0.5 ml of triethylamine is then added, and the mixture is diluted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated in vacuo. After chromatographing the crude product on silica gel using a hexane-ethyl acetate gradient, 7.8 g of 7α-(5-acetoxypentyl)-11β-fluoro-3-(tetrahydropyran-2-yloxy) oestra-1,3,5(10)-trien-17-one are obtained as a foam.

Workup

  1. washwashed with saturated sodium chloride solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customare obtained as a foam

Sources & evidence

ORD record
ord-ed39373d1a6c4c849c806b71b5e43187
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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