11beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-one → 11beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

HRID 1837241Notes

Reaction equation

HRID 1837241 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].[F:29][C:30]([F:44])([F:43])[C:31]([F:42])([F:41])[C:32]([F:40])([F:39])[C:33]([F:38])([F:37])[CH:34](I)[CH3:35]>CN1CCCC1=O>[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])[CH2:35][CH2:34][C:33]([F:38])([F:37])[C:32]([F:40])([F:39])[C:31]([F:42])([F:41])[C:30]([F:44])([F:43])[F:29]

Participants

4

Reactant 2

HCID 1587066511beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-oneHCID 22602436HCID 22602436, compound

Product 1

HCID 8658764411beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

276 mg of 11β-fluoro-3-hydroxy-7α-(5-(methyl-amino)-pentyl)-estra-1,3,5(10)-trien-17-one is dissolved in 3 ml of N-methylpyrrolidone, mixed with 0.6 ml of 1,1,1,2,2,3,3,4,4-nonafluor-5-iodo-hexane and heated for 1.5 hours at a bath temperature of 80° C. For working-up, the reaction mixture is cooled to room temperature, stirred into saturated common salt solution, extracted with ethyl acetate, the organic phases are washed with water, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Preparative column chromatography on silica gel with a methylene chloride-methanol gradient provides 176 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one.

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washthe organic phases are washed with water
  4. customdried on magnesium sulfate
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-204063713d73435babd0e9f9e4c2150d
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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