Sodium Chloride → 11beta-Fluoro-7alpha-{6-[methyl-(7,7,8,8,8-pentafluor-octyl)-amino]-hexyl}-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837246Notes

Reaction equation

HRID 1837246 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][CH:16]2[OH: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][CH2:26]I.[CH3:29][NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39].[Cl-].[Na+]>CN1CCCC1=O>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH: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][CH2:26][N:30]([CH3:29])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([F:42])([F:43])[C:38]([F:39])([F:40])[F:41]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 17910986Methyl-(7,7,8,8,8-pentafluor-octyl)-amineHCID 6991777211beta-Fluor-7alpha-(6-iodohexyl)-estra-1,3,5(10)-triene-3,17-diol

Product 1

HCID 1587065911beta-Fluoro-7alpha-{6-[methyl-(7,7,8,8,8-pentafluor-octyl)-amino]-hexyl}-estra-1,3,5(10)-triene-3,17beta-diolYield 69%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 690 mg of 11β-fluor-7α-(6-iodohexyl)-estra-1,3,5(10)-triene-3,17-diol in 15 ml of 1-methyl-2-pyrrolidinone is stirred with 810 mg of methyl-(7,7,8,8,8-pentafluor-octyl)-amine for 3 hours at a bath temperature of 80° C. For working-up, the batch is added to saturated sodium chloride solution, extracted with ether, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol/ammonia (25%). 576 mg of 11β-fluoro-7α-{6-[methyl-(7,7,8,8,8-pentafluor-octyl)-amino]-hexyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+42° (c=0.5 in CHCl3).

Workup

  1. extractionextracted with ether
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with dichloromethane/methanol/ammonia (25%)

Sources & evidence

ORD record
ord-1c7fa8314ec34c0ca45031564f43754b
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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