17beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3,5-dibenzyloxyphenyl)-2-propenyl)-5alpha-androstan-3-one → 17beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3,5-dihydroxyphenyl)propyl)-5alpha-androstan-3-one

HRID 1744792Notes

Reaction equation

HRID 1744792 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH:30]=[CH:31][C:32]1[CH:37]=[C:36]([O:38]CC2C=CC=CC=2)[CH:35]=[C:34]([O:46]CC2C=CC=CC=2)[CH:33]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[C:34]([OH:46])[CH:35]=[C:36]([OH:38])[CH:37]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 1

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

Product 1

HCID 6962692817beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3,5-dihydroxyphenyl)propyl)-5alpha-androstan-3-oneYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The resulting 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3,5-dibenzyloxyphenyl)-2-propenyl)-5α-androstan-3-one was dissolved in ethyl acetate (3 ml) and stirred in the presence of 10% palladium/carbon (50 mg) at 25° C. for 4 days under hydrogen atmosphere. After the reaction mixture was filtered and evaporated under reduced pressure to remove the solvent, the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1) to give 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3,5-dihydroxyphenyl)propyl)-5α-androstan-3-one (107.5 mg, yield 43%).

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. customevaporated under reduced pressure
  3. customto remove the solvent
  4. customthe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-af589ffb4fb1432a8fc277d7143b8be5
Source dataset
uspto-grants-2006_03
Patent number
US07018993B2

Reaction notes

Loading…