Ethyl 11-[3,17beta-bis(benzyloxy)estra-1,3,5(10), 9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoate → Ethyl 11-(3,17beta-dihydroxyestra-1,3,5(10)-trien-11beta-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoate

HRID 460478Notes

Reaction equation

HRID 460478 reaction equation
C([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][C:22]=3[CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]([CH2:42][CH2:43][C:44]([F:56])([F:55])[C:45]([F:54])([F:53])[C:46]([F:52])([F:51])[C:47]([F:50])([F:49])[F:48])[C:37]([O:39][CH2:40][CH3:41])=[O:38])([CH3:20])[C@@H:18]([O:57]CC3C=CC=CC=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)C1C=CC=CC=1>CO.O1CCCC1.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][C@@H:22]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]([CH2:42][CH2:43][C:44]([F:55])([F:56])[C:45]([F:53])([F:54])[C:46]([F:51])([F:52])[C:47]([F:48])([F:49])[F:50])[C:37]([O:39][CH2:40][CH3:41])=[O:38])([CH3:20])[C@@H:18]([OH:57])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

5

Reactant 1

HCID 86588531Ethyl 11-[3,17beta-bis(benzyloxy)estra-1,3,5(10), 9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoate

Product 1

HCID 86588532Ethyl 11-(3,17beta-dihydroxyestra-1,3,5(10)-trien-11beta-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoateYield 71.4%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 11-[3,17β-bis(benzyloxy)estra-1,3,5(10),9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoate (500 mg, 0.55 mmol) was dissolved in a mixed solvent of methanol (10 ml) and tetrahydrofuran (1 ml), followed by addition of palladium hydroxide/carbon (150 mg) at room temperature. After purging with hydrogen, the reaction mixture was stirred for 23 hours at room temperature and then filtered. The solvent was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→3/1→2/1) to give ethyl 11-(3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoate (287 mg, Yield 71%).

Workup

  1. customAfter purging with hydrogen
  2. filtrationfiltered
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→3/1→2/1)

Sources & evidence

ORD record
ord-e41b4d6bcedc4b4aa008603b273afe36
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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