Benzene, 1-ethenyl-3,5-bis(phenylmethoxy)- → 17beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3,5-dibenzyloxyphenyl)-2-propenyl)-5alpha-androstan-3-one

HRID 1744791Notes

Reaction equation

HRID 1744791 reaction equation
[CH2:1]([C@@H:4]1[CH2:21][C@@H:20]2[C@:15]([CH3:23])([CH2:16][CH2:17][C:18](=[O:22])[CH2:19]2)[C@@H:14]2[C@@H:5]1[C@H:6]1[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C@@H:9]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:8][CH2:7]1)[CH:2]=[CH2:3].[CH2:32]([O:39][C:40]1[CH:41]=[C:42]([CH:45]=[C:46]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:47]=1)C=C)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl.C(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1.Cl[Ru]Cl>[Si:25]([O:24][C@H:9]1[CH2:8][CH2:7][C@H:6]2[C@H:5]3[C@H:14]([CH2:13][CH2:12][C@:10]12[CH3:11])[C@:15]1([CH3:23])[C@H:20]([CH2:19][C:18](=[O:22])[CH2:17][CH2:16]1)[CH2:21][C@H:4]3[CH2:1][CH:2]=[CH:3][C:42]1[CH:45]=[C:46]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:47]=[C:40]([O:39][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:41]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 21672619Benzene, 1-ethenyl-3,5-bis(phenylmethoxy)-HCID 696269387alpha-Allyl-17beta-(tert-butyldimethylsilyloxy)-5alpha-androstan-3-one

Product 1

HCID 6962705617beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3,5-dibenzyloxyphenyl)-2-propenyl)-5alpha-androstan-3-one

Reagents, catalysts & solvents 2

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphaneCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

Under argon atmosphere, 7α-allyl-17β-(tert-butyldimethylsilyloxy)-5α-androstan-3-one (200 mg), 3,5-dibenzyloxystyrene (285 mg) and benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium (37 mg) were dissolved in methylene chloride (2.5 ml) and stirred at 30° C. for 14 hours. After evaporation under reduced pressure to remove the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3,5-dibenzyloxyphenyl)-2-propenyl)-5α-androstan-3-one.

Workup

  1. customAfter evaporation under reduced pressure
  2. customto remove the solvent
  3. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-79701daf5f684d22878e45f58f0c6585
Source dataset
uspto-grants-2006_03
Patent number
US07018993B2

Reaction notes

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