1-Iodononane → 11beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-nonyl-amino]pentyl}oestra-1,3,5(10)-trien-17-one

HRID 1838905Notes

Reaction equation

[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O: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][NH:26][CH3:27].I[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]C.[C:39](=O)([O-])O.[Na+]>CN(C=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O: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][N:26]([CH3:39])[CH2:27][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

Conditions

Temperature: 100 °C

Procedure

526 mg of 11β-fluoro-3-hydroxy-7α-[5-(methylamino)-pentyl]oestra-1,3,5(10)-trien-17-one and 127 mg of iodononane are dissolved in 5 ml of anhydrous DMF and stirred at a bath temperature of 100° C. for 4 h. For work-up, the mixture is added to half-saturated sodium hydrogencarbonate solution, extracted 3 times with methylene chloride, dried over magnesium sulphate and concentrated in vacuo. Preparative column chromatography yields 85 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-nonyl-amino]pentyl}oestra-1,3,5(10)-trien-17-one as a foam.

Workup

extractionextracted 3 times with methylene chloride
dry with materialdried over magnesium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f9b0a4700c0f4d8cb4c4ccafeaa720cc
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677324B1

Reaction notes

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