Diisopropylethylamine → 11beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}estra-1,3,5(10)-trien-3-ol-17-one

HRID 1744787Notes

Reaction equation

HRID 1744787 reaction equation
C(N(C(C)C)C(C)C)C.[F:10][C@H:11]1[CH2:28][C@@:26]2([CH3:27])[C@@H:22]([CH2:23][CH2:24][C@@H:25]2[OH:29])[C@H:21]2[C@H:12]1[C:13]1[CH:14]=[CH:15][C:16]([OH:56])=[CH:17][C:18]=1[CH2:19][C@H:20]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:55])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([F:54])([F:53])[C:43]([F:52])([F:51])[C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46]>CS(C)=O.C(OCC)(=O)C>[F:10][C@H:11]1[CH2:28][C@@:26]2([CH3:27])[C@@H:22]([CH2:23][CH2:24][C:25]2=[O:29])[C@H:21]2[C@H:12]1[C:13]1[CH:14]=[CH:15][C:16]([OH:56])=[CH:17][C:18]=1[CH2:19][C@H:20]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:55])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([F:53])([F:54])[C:43]([F:51])([F:52])[C:44]([F:49])([F:50])[C:45]([F:46])([F:47])[F:48]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 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

Product 1

HCID 1209588811beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}estra-1,3,5(10)-trien-3-ol-17-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.5 ml of ethyldiisopropylamine is added in drops at 10° C. to a solution of 1.23 g of pyridine sulfur trioxide complex in 10 ml of dried dimethyl sulfoxide. Then, 1.72 g of 11β-fluoro-7α-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-estra-1,3,5(10)-triene-3,17β-diol (compound No. Z9) as well as another 10 ml of dried dimethyl sulfoxide are added and stirred for 30 minutes at room temperature. Then, it is diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, water and sodium chloride solution, dried on sodium sulfate, evaporated to the dry state in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 11β-Fluoro-7α-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}estra-1,3,5(10)-trien-3-ol-17-one, [α]D=+58.2°, in chloroform, is obtained.

Workup

  1. washwashed with saturated sodium bicarbonate solution, water and sodium chloride solution
  2. customdried on sodium sulfate
  3. customevaporated to the dry state in a vacuum
  4. customchromatographed on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-669a2830498c4d76a52e87dde7c0db3e
Source dataset
uspto-grants-2006_03
Patent number
US07018994B2

Reaction notes

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