Sodium Chloride → 11beta-Fluoro-7alpha-{5-[(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluor-undecyl)-methyl-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837240Notes

Reaction equation

HRID 1837240 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.[F:28][C:29]([F:57])([C:35]([F:56])([F:55])[C:36]([F:54])([F:53])[C:37]([F:52])([F:51])[C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])[CH2:30][CH2:31][CH2:32][NH:33][CH3:34].[Cl-].[Na+].[CH3:60]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: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][CH2:34][N:33]([CH2:32][CH2:31][CH2:30][C:29]([F:57])([F:28])[C:35]([F:55])([F:56])[C:36]([F:53])([F:54])[C:37]([F:51])([F:52])[C:38]([F:49])([F:50])[C:39]([F:47])([F:48])[C:40]([F:45])([F:46])[C:41]([F:44])([F:43])[F:42])[CH3:60]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 13387N-methyl-2-pyrrolidoneHCID 23497244(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluor-undecyl)-methyl-amineHCID 699180487alpha-(5-Bromopentyl)-11beta-fluor-estra-1,3,5(10)-triene-3,17-diol

Product 1

HCID 1585865111beta-Fluoro-7alpha-{5-[(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluor-undecyl)-methyl-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

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 1.47 g of (4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluor-undecyl)-methyl-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 ethyl acetate/methanol. 524 mg of 11β-fluoro-7α-{5-[(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluor-undecyl)-methyl-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+24° (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 ethyl acetate/methanol

Sources & evidence

ORD record
ord-8b68de437dee4cad9193b32d70abb51a
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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