Potassium Carbonate → 11beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

HRID 1837237Notes

Reaction equation

HRID 1837237 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[F:35][C:36]([F:45])([F:44])[C:37]([F:43])([F:42])[CH2:38][CH2:39][CH2:40]I>C(C(C)=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH2:40][CH2:39][CH2:38][C:37]([F:43])([F:42])[C:36]([F:45])([F:44])[F:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120170571,1,1,2,2-Pentafluoro-5-iodopentaneHCID 1587066511beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-one

Product 1

HCID 1587066911beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

500 mg of 11β-fluoro-3-hydroxy-7α-(5-(methyl-amino)-pentyl)-estra-1,3,5(10)-trien-17-one is dissolved in 15 ml of ethylmethylketone, mixed with 1.1 g of potassium carbonate and 1.5 ml of 1,1,1,2,2-pentafluor-5-iodo-pentane and refluxed for 2.5 hours. For working-up, the reaction mixture is cooled to room temperature, stirred into saturated common salt solution, extracted with ethyl acetate, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Preparative column chromatography on silica gel with a methylene chloride-methanol gradient provides 397 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-ea087405f3954a98ae5272adb2d3655b
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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