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

HRID 1837243Notes

Reaction equation

HRID 1837243 reaction equation
Br[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])[CH:12]([OH:27])[CH2:11][CH2:10]1.[CH3:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38].[Cl-].[Na+]>CN1CCCC1=O>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]2[OH: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:29]([CH3:28])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([F:41])([F:42])[C:37]([F:38])([F:39])[F:40]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 17910986Methyl-(7,7,8,8,8-pentafluor-octyl)-amineHCID 699180487alpha-(5-Bromopentyl)-11beta-fluor-estra-1,3,5(10)-triene-3,17-diol

Product 1

HCID 1585865311beta-Fluoro-7alpha-{5-[methyl-(7,7,8,8,8-pentafluor-octyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diolYield 94.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 466 mg of 7α-(5-bromopentyl)-11β-fluor-estra-1,3,5(10)-triene-3,17-diol in 10 ml of 1-methyl-2-pyrrolidinone is stirred with 702 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 ethyl acetate, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 595 mg of 11β-fluoro-7α-{5-[methyl-(7,7,8,8,8-pentafluor-octyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+39° (c=0.5 in CHCl3).

Workup

  1. extractionextracted with ethyl acetate
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-cd48ba1e5bbf41af8922c0e0e60aa721
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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