HCID 15870673, compound → HCID 86587649, compound

HRID 1837253Notes

Reaction equation

HRID 1837253 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:27])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]I.[F:28][C:29]([C:34]([F:55])([F:54])[C:35]([F:53])([F:52])[C:36]([F:51])([F:50])[C:37]([F:49])([F:48])[C:38]([F:47])([F:46])[C:39]([F:45])([F:44])[C:40]([F:43])([F:42])[F:41])=[CH:30][CH2:31][NH:32][CH3:33]>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:27])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:32]([CH2:31][CH:30]=[C:29]([F:28])[C:34]([F:54])([F:55])[C:35]([F:52])([F:53])[C:36]([F:50])([F:51])[C:37]([F:48])([F:49])[C:38]([F:46])([F:47])[C:39]([F:44])([F:45])[C:40]([F:43])([F:42])[F:41])[CH3:33]

Participants

4

Reactant 2

HCID 15870673HCID 15870673, compoundHCID 54041103HCID 54041103, compound

Product 1

HCID 86587649HCID 86587649, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

880 mg of 11β-fluoro-3-hydroxy-7α-(5-iodopentyl)-estra-1,3,5(10)-trien-17-one and 1.83 g of (3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-hexadecafluoro-dec-2-enyl)-methyl-amine are dissolved in 20 ml of N-methylpyrrolidone and stirred for 1 hour at a bath temperature of 80° C. After the reaction solution is cooled to room temperature, the batch is added to saturated common salt solution, extracted with diethyl ether, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with ethyl acetate as an eluant, 1.2 g of 11β-fluoro-7α-{5-[(3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-hexadecafluoro-dec-2-enyl)-methyl-amino]-pentyl}-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. temperatureAfter the reaction solution is cooled to room temperature
  2. additionthe batch is added to saturated common salt solution
  3. extractionextracted with diethyl ether
  4. customdried
  5. concentrationconcentrated by evaporation in a vacuum
  6. customAfter the crude product is chromatographed on silica gel with ethyl acetate as an eluant

Sources & evidence

ORD record
ord-64a576f3168444579aed7329ca09cd11
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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