Lithium iodide → 11beta-Fluoro-3-hydroxy-7alpha-{5-[2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidin-1-yl]-pentyl}-estra-1,3,5(10)-trien-17-one

HRID 650363Notes

Reaction equation

HRID 650363 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1.[I-].[Li+].[F:30][C:31]([F:46])([C:42]([F:45])([F:44])[F:43])[CH2:32][CH2:33][CH2:34][S:35][CH2:36][C@@H:37]1[CH2:41][CH2:40][CH2:39][NH:38]1>CN1CCCC1=O>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C:12]2=[O:27])[C@H:8]2[C@H:17]1[C:18]1[CH:19]=[CH:20][C:21]([OH:25])=[CH:22][C:23]=1[CH2:24][C@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:38]1[CH2:39][CH2:40][CH2:41][CH:37]1[CH2:36][S:35][CH2:34][CH2:33][CH2:32][C:31]([F:46])([F:30])[C:42]([F:43])([F:44])[F:45]

Participants

5

Reactant 3

HCID 66321Lithium iodideHCID 57069197(2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidineHCID 68949346HCID 68949346, compound

Product 1

HCID 5725928411beta-Fluoro-3-hydroxy-7alpha-{5-[2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidin-1-yl]-pentyl}-estra-1,3,5(10)-trien-17-oneYield 44.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 785.9 mg of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one in 7 ml of N-methyl-2-pyrrolidinone is mixed with 535.5 mg of lithium iodide and 520 mg of (2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidine, and it is stirred for 2.5 hours at a bath temperature of 100° C. Then, it is poured onto water, extracted 3 times with diethyl ether, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 525 mg of pure 11β-fluoro-3-hydroxy-7α-{5-[2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidin-1-yl]-pentyl}-estra-1,3,5(10)-trien-17-one is obtained. [α]D22=+29.3° (c=0.5% in chloroform).

Workup

  1. additionThen, it is poured onto water
  2. extractionextracted 3 times with diethyl ether
  3. washwashed neutral
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customchromatographed on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-0696b9ad2abe4c09a27f70744d0fd07f
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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