Sodium Chloride → 11beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1838913Notes

Reaction equation

HRID 1838913 reaction equation
BrC[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:48])([F:47])[C:37]([F:46])([F:45])[C:38]([F:44])([F:43])[C:39]([F:42])([F:41])[F:40].[Cl-].[Na+].[CH3:51]N1CCCC1=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:23]=[CH:22][C:21]([OH:25])=[CH:20][C:19]=1[CH2:24][C@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:28][N:29]([CH3:51])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([F:47])([F:48])[C:37]([F:45])([F:46])[C:38]([F:43])([F:44])[C:39]([F:40])([F:41])[F:42]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 13387N-methyl-2-pyrrolidoneHCID 12095891Methyl-(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amineHCID 699180487alpha-(5-Bromopentyl)-11beta-fluor-estra-1,3,5(10)-triene-3,17-diol

Product 1

HCID 1585865411beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

Procedure

A solution of 466 mg of 7α-(5-bromopentyl)-11β-fluorooestra-1,3,5(10)-triene-3,17-diol in 10 ml of 1-methyl-2-pyrrolidinone is stirred at a bath temperature of 80° C. for 3 hours with 1.0 g of methyl-(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amine. For work-up, the mixture is added to saturated sodium chloride solution, extracted with ether, dried over sodium sulphate, concentrated in vacuo and the residue is chromatographed on silica gel using ethyl acetate/methanol. 546 mg of 11β-fluoro-7α-{5-[methyl-(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-oestra-1,3,5(10)triene-3, 17β-diol are obtained as a foam, [α]D=+39° (c=0.5 in CHCl3)

Workup

  1. extractionextracted with ether
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-dc258ae655f44d10a20ff21d705112e2
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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