Potassium Carbonate → 11beta-Fluoro-7alpha-(5-hydroxypentyl)-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-one

HRID 1838884Notes

Reaction equation

HRID 1838884 reaction equation
C([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:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]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:35])([CH3:17])[C:15](=[O:36])[CH2:14][CH2:13]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:35][C@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[O:36])[C@H:11]2[C@H:20]1[C:21]1[CH:22]=[CH:23][C:24]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)=[CH:25][C:26]=1[CH2:27][C@H:10]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 229418067alpha-(5-Acetoxypentyl)-11beta-fluoro-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-one

Product 1

HCID 2294178011beta-Fluoro-7alpha-(5-hydroxypentyl)-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-oneYield 103.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7.4 g of 7α- (5-acetoxypentyl)-11β-fluoro-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-one are stirred with 1.8 g of potassium carbonate at room temperature in 370 ml of methanol and 37 ml of water. After 3 h, the reaction mixture is added to ice-water. The precipitated product is filtered off with suction, dissolved in ethyl acetate, and the solution is washed with water until neutral, dried and concentrated in vacuo. 7.0 g of 11β-fluoro-7α-(5-hydroxypentyl)-3-(tetrahydropyran-2-yloxy)oestra-1,3,5(10)-trien-17-one are obtained as a foam.

Workup

  1. filtrationThe precipitated product is filtered off with suction
  2. dissolutiondissolved in ethyl acetate
  3. washthe solution is washed with water until neutral,
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-592ae5f587a548bbb2c2c773e612b14f
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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